Organometallic complex, and light-emitting device and electronic appliance using the same

ABSTRACT

In a general formula (1), each of R 1  and R 2  represents any one of hydrogen, an alkyl group, a halogen group, —CF3, an alkoxy group, and an aryl group. M represents an element that belongs to Group 9 or Group 10. Here, an alkyl group having 1 to 4 carbon atoms is preferable in the alkyl group. A fluoro group is particularly preferable in the halogen group. An alkoxy group having 1 to 4 carbon atoms is preferable in the alkoxy group. A phenyl group is particularly preferable in the aryl group. Iridium is particularly preferable among the elements that belong to Group 9, and platinum is particularly preferable among the elements that belong to Group 10. The general formula (1) is inserted.

This application is a continuation of U.S. application Ser. No.11/909,130 filed on Sep. 19, 2007, now U.S. Pat. No. 8,053,974, which isthe US national stage of PCT/JP2006/306377 filed on Mar. 22, 2006.

TECHNICAL FIELD

The present invention relates to a substance which can emit light bycurrent excitation, and specifically, an organometallic complex whichemits light by current excitation. Furthermore, the present inventionrelates to a light-emitting element and a light-emitting device, each ofwhich uses the substance.

BACKGROUND ART

A light-emitting element including a layer containing a light-emittingsubstance between a pair of electrodes is used as a pixel, a lightsource, or the like, and is provided in a light-emitting device such asa display device or a lightening system. An excited light-emittingsubstance emits fluorescence or phosphorescence when current is appliedbetween a pair of electrodes of a light-emitting element.

In theory, internal quantum efficiency of phosphorescence is about threetimes as large as that of fluorescence in a case of current excitation,when fluorescence and phosphorescence are compared with each other.Therefore, it is considered that light-emitting efficiency is increasedby using a light-emitting substance which emits phosphorescence thanusing a light-emitting substance which emits fluorescence, and asubstance which emits phosphorescence has been developed so far.

For example, a metal complex having iridium as its central metal isdisclosed in Patent Document 1. According to Patent Document 1,high-efficiency organic light-emitting device can be obtained by usingthe metal complex.

As described above, a light-emitting element which operates efficientlycan be obtained by using a metal complex. However, metal such as iridiumor platinum which is used as a central metal of a metal complex isexpensive. Therefore, there is a problem that cost of raw materials formanufacturing a light-emitting element is high in a case of using ametal complex.

-   Patent Document 1: Published Japanese translation of PCT    international application, No. 2005-506361

DISCLOSURE OF INVENTION

It is an object of the present invention to provide an organometalliccomplex which can emit phosphorescence. It is also an object of thepresent invention to provide an organometallic complex which can besynthesized with high yield. In addition, it is an object of the presentinvention to provide a light-emitting element which emits lightefficiently and can be manufactured at low cost.

One aspect of the present invention is an organometallic complexincluding a structure represented by a general formula (1).

In the general formula (1), each of R¹ and R² represents any one ofhydrogen, an alkyl group, a halogen group, —CF₃, an alkoxy group, and anaryl group. M represents an element that belongs to Group 9 or Group 10of the periodic table. Here, an alkyl group having 1 to 4 carbon atomsis preferable in the alkyl group, and particularly, any group selectedfrom a methyl group, an ethyl group, an isopropyl group, a sec-butylgroup, and a tert-butyl group is preferable. A fluoro group isparticularly preferable in the halogen group since chemical stability isimproved. Also, an alkoxy group having 1 to 4 carbon atoms is preferablein the alkoxy group, and particularly, a methoxy group is preferable. Aphenyl group is particularly preferable in the aryl group. Iridium isparticularly preferable among the elements that belong to Group 9, andplatinum is particularly preferable among the elements that belong toGroup 10.

Another aspect of the present invention is an organometallic complexrepresented by a general formula (2).

In the general formula (2), each of R³ and R⁴ represents any one ofhydrogen, an alkyl group, a halogen group, —CF₃, an alkoxy group, and anaryl group. M represents an element that belongs to Group 9 or Group 10of the periodic table. Also, L represents any one of a monoanionicligand having a beta-diketone structure, a monoanionic bidentate chelateligand having a carboxyl group, and a monoanionic bidentate chelateligand having a phenol hydroxyl group. Here, an alkyl group having 1 to4 carbon atoms is preferable in the alkyl group, and particularly, anygroup selected from a methyl group, an ethyl group, an isopropyl group,a sec-butyl group, and a tert-butyl group is preferable. A fluoro groupis particularly preferable in the halogen group since chemical stabilityis improved. Also, an alkoxy group having 1 to 4 carbon atoms ispreferable in the alkoxy group, and particularly, a methoxy group ispreferable. A phenyl group is particularly preferable in the aryl group.Iridium is particularly preferable among the elements that belong toGroup 9, and platinum is particularly preferable among the elements thatbelong to Group 10. Further, n=2 when M is an element that belongs toGroup 9, and n=1 when M is an element that belongs to Group 10.

Another aspect of the present invention is an organometallic complexincluding a structure represented by a general formula (3).

In the general formula (3), each of R⁵ and R⁶ represents any one ofhydrogen, an alkyl group, a halogen group, —CF₃, an alkoxy group, and anaryl group. Here, an alkyl group having 1 to 4 carbon atoms ispreferable in the alkyl group, and particularly, any group selected froma methyl group, an ethyl group, an isopropyl group, a sec-butyl group,and a tert-butyl group is preferable. A fluoro group is particularlypreferable in the halogen group since chemical stability is improved.Also, an alkoxy group having 1 to 4 carbon atoms is preferable in thealkoxy group, and particularly, a methoxy group is preferable. A phenylgroup is particularly preferable in the aryl group.

Another feature of the present invention is an organometallic complexincluding a structure represented by a general formula (4).

In the general formula (4), each of R⁷ and R⁸ represents any one ofhydrogen, an alkyl group, a halogen group, —CF₃, an alkoxy group, and anaryl group. L represents any one of a monoanionic ligand having abeta-diketone structure, a monoanionic bidentate chelate ligand having acarboxyl group, and a monoanionic bidentate chelate ligand having aphenol hydroxyl group. Here, an alkyl group having 1 to 4 carbon atomsis preferable in the alkyl group, and particularly, any group selectedfrom a methyl group, an ethyl group, an isopropyl group, a sec-butylgroup, and tert-butyl group is preferable. A fluoro group isparticularly preferable in the halogen group since chemical stability isimproved. Also, an alkoxy group having 1 to 4 carbon atoms is preferablein the alkoxy group, and particularly, a methoxy group is preferable. Aphenyl group is particularly preferable in the aryl group.

As for organometallic complexes represented by the general formulas (2)and (4), it is preferable that L be any ligand selected from ligandsrepresented by following structural formulas (1) to (7) specifically.

Another aspect of the present invention is an organometallic complexincluding a structure represented by a general formula (5).

In the general formula (5), each of R⁹ to R¹² represents any one ofhydrogen, an alkyl group, a halogen group, —CF₃, an alkoxy group, and anaryl group. M represents an element that belongs to Group 9 or Group 10of the periodic table. Here, an alkyl group having 1 to 4 carbon atomsis preferable in the alkyl group, and particularly, any group selectedfrom a methyl group, an ethyl group, an isopropyl group, a sec-butylgroup, and a tert-butyl group is preferable. A fluoro group isparticularly preferable in the halogen group since chemical stability isimproved. Also, an alkoxy group having 1 to 4 carbon atoms is preferablein the alkoxy group, and particularly, a methoxy group is preferable. Aphenyl group is particularly preferable in the aryl group. Iridium isparticularly preferable among the elements that belong to Group 9, andplatinum is particularly preferable among the elements that belong toGroup 10.

Another aspect of the present invention is an organometallic complexrepresented by a general formula (6).

In the general formula (6), each of R¹³ to R¹⁶ represents any one ofhydrogen, an alkyl group, a halogen group, —CF₃, an alkoxy group, and anaryl group. M represents an element that belongs to Group 9 or Group 10of the periodic table. Also, L represents any one of a monoanionicligand having a beta-diketone structure, a monoanionic bidentate chelateligand having a carboxyl group, and a monoanionic bidentate chelateligand having a phenol hydroxyl group. Here, an alkyl group having 1 to4 carbon atoms is preferable in the alkyl group, and particularly, anygroup selected from a methyl group, an ethyl group, an isopropyl group,and a sec-butyl group is preferable. A fluoro group is particularlypreferable in the halogen group since chemical stability is improved.Also, an alkoxy group having 1 to 4 carbon atoms is preferable in thealkoxy group, and particularly, a methoxy group is preferable. A phenylgroup is particularly preferable in the aryl group. Iridium isparticularly preferable among the elements that belong to Group 9, andplatinum is particularly preferable among the elements that belong toGroup 10. Further, n=2 when M is an element that belongs to Group 9, andn=1 when M is an element that belongs to Group 10.

Another aspect of the present invention is an organometallic complexincluding a structure represented by a general formula (7).

In the general formula (7), each of R¹⁷ to R²⁰ represents any one ofhydrogen, an alkyl group, a halogen group, —CF₃, an alkoxy group, and anaryl group. Here, an alkyl group having 1 to 4 carbon atoms ispreferable in the alkyl group, and particularly, any group selected froma methyl group, an ethyl group, an isopropyl group, a sec-butyl group,and a tert-butyl group is preferable. A fluoro group is particularlypreferable in the halogen group since chemical stability is improved.Also, an alkoxy group having 1 to 4 carbon atoms is preferable in thealkoxy group, and particularly, a methoxy group is preferable. A phenylgroup is particularly preferable in the aryl group.

Another aspect of the present invention is an organometallic complexincluding a structure represented by a general formula (8).

In the general formula (8), each of R²¹ and R²⁴ represents any one ofhydrogen, an alkyl group, a halogen group, —CF₃, an alkoxy group, and anaryl group. L represents any one of a monoanionic ligand having abeta-diketone structure, a monoanionic bidentate chelate ligand having acarboxyl group, and a monoanionic bidentate chelate ligand having aphenol hydroxyl group. Here, an alkyl group having 1 to 4 carbon atomsis preferable in the alkyl group, and particularly, any group selectedfrom a methyl group, an ethyl group, an isopropyl group, a sec-butylgroup, and a tert-butyl group is preferable. A fluoro group isparticularly preferable in the halogen group since chemical stability isimproved. Also, an alkoxy group having 1 to 4 carbon atoms is preferablein the alkoxy group, and particularly, a methoxy group is preferable. Aphenyl group is particularly preferable in the aryl group.

As for an organometallic complex represented by the general formulas (6)and (8), it is preferable that L be any ligand selected from ligandsrepresented by following structural formulas (1) to (7) specifically.

Another aspect of the present invention is an organometallic complexincluding a structure represented by a general formula (9).

In the general formula (9), each of R²⁵ to R³⁰ represents any one ofhydrogen, an alkyl group, a halogen group, —CF₃, and an alkoxy group. Mrepresents an element that belongs to Group 9 or Group 10. Here, analkyl group having 1 to 4 carbon atoms is preferable in the alkyl group,and particularly, any group selected from a methyl group, an ethylgroup, an isopropyl group, a sec-butyl group, and a tert-butyl group ispreferable. A fluoro group is particularly preferable in the halogengroup since chemical stability is improved. Also, an alkoxy group having1 to 4 carbon atoms is preferable in the alkoxy group, and particularly,a methoxy group is preferable. Iridium is particularly preferable amongthe elements that belong to Group 9, and platinum is particularlypreferable among the elements that belong to Group 10.

Another aspect of the present invention is an organometallic complexrepresented by a general formula (10).

In the general formula (10), each of R³¹ to R³⁶ represents any one ofhydrogen, an alkyl group, a halogen group, —CF₃, and an alkoxy group. Mrepresents an element that belongs to Group 9 or Group 10 of theperiodic table. Also, L represents any one of a monoanionic ligandhaving a beta-diketone structure, a monoanionic bidentate chelate ligandhaving a carboxyl group, and a monoanionic bidentate chelate ligandhaving a phenol hydroxyl group. Here, an alkyl group having 1 to 4carbon atoms is preferable in the alkyl group, and particularly, anygroup selected from a methyl group, an ethyl group, an isopropyl group,a sec-butyl group, and a tert-butyl group is preferable. A fluoro groupis particularly preferable in the halogen group since chemical stabilityis improved. Also, an alkoxy group having 1 to 4 carbon atoms ispreferable in the alkoxy group, and particularly, a methoxy group ispreferable. Iridium is particularly preferable among the elements thatbelong to Group 9, and platinum is particularly preferable among theelements that belong Group 10. Further, n=2 when M is an element thatbelongs to Group 9, and n=1 when M is an element that belongs to Group10.

Another aspect of the present invention is an organometallic complexincluding a structure represented by a general formula (11).

In the general formula (11), each of R³⁷ to R⁴² represents any one ofhydrogen, an alkyl group, a halogen group, —CF₃, and an alkoxy group.Here, an alkyl group having 1 to 4 carbon atoms is preferable in thealkyl group, and particularly, any group selected from a methyl group,an ethyl group, an isopropyl group, a sec-butyl group, and a tert-butylgroup is preferable. A fluoro group is particularly preferable in thehalogen group since chemical stability is improved. Also, an alkoxygroup having 1 to 4 carbon atoms is preferable in the alkoxy group, andparticularly, a methoxy group is preferable.

Another aspect of the present invention is an organometallic complexincluding a structure represented by a general formula (12).

In the general formula (12), each of R⁴³ to R⁴⁸ represents any one ofhydrogen, an alkyl group, a halogen group, —CF₃, and an alkoxy group. Lrepresents any one of a monoanionic ligand having a beta-diketonestructure, a monoanionic bidentate chelate ligand having a carboxylgroup, and a monoanionic bidentate chelate ligand having a phenolhydroxyl group. Here, an alkyl group having 1 to 4 carbon atoms ispreferable in the alkyl group, and particularly, any group selected froma methyl group, an ethyl group, an isopropyl group, a sec-butyl group,and tert-butyl group is preferable. A fluoro group is particularlypreferable in the halogen group since chemical stability is improved.Also, an alkoxy group having 1 to 4 carbon atoms is preferable in thealkoxy group, and particularly, a methoxy group is preferable.

As for organometallic complexes represented by the general formulas (10)and (12), it is preferable that L be any ligand selected from ligandsrepresented by following structural formulas (1) to (7) specifically.The ligands represented by the structural formulas (1) to (7) aremonoanionic ligands.

Another aspect of the present invention is that, as for theorganometallic complex including the structure represented by thegeneral formula (1), each of R¹ and R² is hydrogen or fluorine, and M isiridium or platinum, particularly.

Another aspect of the present invention is that, as for anorganometallic complex represented by the general formula (2), each ofR³ and R⁴ is hydrogen or fluorine, M is iridium or platinum, and L isany one of an acetylacenato ligand, a picolinato ligand and atetrakis(1-pyrazolyl)borate ligand, particularly. Specifically, it is anorganometallic complex represented by a general formula (13).

In the general formula (13), each of R⁶¹ and R⁶² represents hydrogen orfluorine. M represents iridium or platinum. Also, L represents a ligandrepresented by any one of structural formulas (36) to (38). Further, n=2when M is iridium, and n=1 when M is platinum.

It is to be noted that a dashed line included in each of generalformulas described above denotes a coordinate bond.

Another aspect of the present invention is a light-emitting elementcontaining an organometallic complex represented by any one of thegeneral formulas (1) to (13). The light-emitting element includes alayer containing an organometallic complex represented by any one of thegeneral formulas (1) to (13) between electrodes, and it is preferablethat the light-emitting element include a structure in which theorganometallic complex represented by any one of the general formulas(1) to (13) emits light when a current is applied between theelectrodes. As described above, a light-emitting element using theorganometallic complex of the present invention as a light-emittingsubstance can obtain phosphorescence; therefore, the light-emittingelement emits light efficiently. Also, the organometallic complex of thepresent invention can be synthesized with high yield and is productive;therefore, a light-emitting element with reduced cost of raw materialscan be manufactured by using the organometallic complex of the presentinvention.

Another aspect of the present invention is a light-emitting device usinga light-emitting element containing an organometallic complexrepresented by any one of the general formulas (1) to (13) as a pixel ora light source. As described above, the light-emitting element of thepresent invention emits light efficiently; therefore, a light-emittingdevice which is driven with low power consumption can be obtained byusing the light-emitting element of the present invention. Also, thelight-emitting element of the present invention can be manufactured atlow cost; therefore a light-emitting device with low production cost andlow price can be obtained by using the light-emitting element of thepresent invention.

By carrying out the present invention, an organometallic complex whichemits phosphorescence can be obtained. Also, an organometallic complexwhich can be synthesized with high yield can be obtained by carrying outthe present invention.

By carrying out the present invention, a light-emitting element whichcan emit phosphorescence and particularly has high internal quantumefficiency can be obtained. Also, a light-emitting element with low costof raw materials can be obtained by carrying out the present invention.

By carrying out the present invention, a light-emitting device whichemits light efficiently and with low production cost can be obtained.

BRIEF DESCRIPTION OF DRAWINGS

In the accompanying drawings:

FIG. 1 is a view explaining one mode of a light-emitting device of thepresent invention;

FIG. 2 is a view explaining a light-emitting device to which the presentinvention is applied;

FIG. 3 is a diagram explaining a circuit included in a light-emittingdevice to which the present invention is applied;

FIG. 4 is a top view of a light-emitting device to which the presentinvention is applied;

FIG. 5 is a view explaining a frame operation of a light-emitting deviceto which the present invention is applied;

FIGS. 6A to 6C are cross-sectional views of a light-emitting device towhich the present invention is applied;

FIG. 7 is a view explaining a light-emitting device to which the presentinvention is applied;

FIGS. 8A to 8C are views showing electronic appliances to which thepresent invention is applied;

FIG. 9 is a chart obtained by analyzing an organometallic complexsynthesized in Synthesis Example 1 by using ¹H-NMR;

FIG. 10 is a graph showing an absorption spectrum and an emissionspectrum of an organometallic complex synthesized in Synthesis Example1;

FIG. 11 is a view explaining a manufacturing method of a light-emittingelement of Embodiment 1.

FIG. 12 is a graph showing a current density vs luminance characteristicwhen a light-emitting device of Embodiment 2 is operated;

FIG. 13 is a graph showing a voltage vs luminance characteristic when alight emitting device of Embodiment 2 is operated;

FIG. 14 is a graph showing a luminance vs current efficiencycharacteristic when a light-emitting device of Embodiment 2 is operated;

FIG. 15 is a graph showing an emission spectrum obtained when alight-emitting device of Embodiment 2 is operated;

FIGS. 16A and 16B are charts obtained by analyzing an organometalliccomplex of the present invention synthesized in Synthesis Example 2 byusing ¹H-NMR;

FIG. 17 is a graph showing an absorption spectrum and an emissionspectrum of an organometallic complex synthesized in Synthesis example2;

FIGS. 18A and 18B are charts obtained by analyzing an organometalliccomplex of the present invention synthesized in Synthesis Example 3 byusing ¹H-NMR;

FIG. 19 is a graph showing an absorption spectrum and an emissionspectrum of an organometallic complex synthesized in Synthesis Example3;

FIGS. 20A and 20B are charts obtained by analyzing an organometalliccomplex of the present invention synthesized in Synthesis Example 4 byusing ¹H-NMR;

FIG. 21 is a graph showing an absorption spectrum and an emissionspectrum of an organometallic complex synthesized in Synthesis Example4;

FIGS. 22A and 22B are charts obtained by analyzing an organometalliccomplex of the present invention synthesized in Synthesis Example 5 byusing ¹H-NMR;

FIG. 23 is a graph showing an absorption spectrum and an emissionspectrum of an organometallic complex synthesized in Synthesis Example5;

FIG. 24 is a view explaining a manufacturing method of a light emittingelement of Embodiments 3 and 4;

FIG. 25 is a graph showing a current density vs luminance characteristicwhen a light-emitting device of Embodiment 3 is operated;

FIG. 26 is a graph showing a voltage vs luminance characteristic when alight-emitting device of Embodiment 3 is operated;

FIG. 27 is a graph showing a luminance vs current efficiencycharacteristic when a light-emitting device of Embodiment 3 is operated;

FIG. 28 is a graph showing an emission spectrum obtained when alight-emitting device of Embodiment 3 is operated;

FIG. 29 is a graph showing a current density vs luminance characteristicwhen a light-emitting device of Embodiment 4 is operated;

FIG. 30 is a graph showing a voltage vs luminance characteristic when alight-emitting device of Embodiment 4 is operated;

FIG. 31 is a graph showing a luminance vs current efficiencycharacteristic when a light-emitting device of Embodiment 4 is operated;

FIG. 32 is a graph showing an emission spectrum obtained when alight-emitting device of Embodiment 4 is operated;

FIG. 33 is a graph showing a current density vs luminance characteristicwhen a light-emitting device of Embodiment 5 is operated;

FIG. 34 is a graph showing a voltage vs luminance characteristic when alight-emitting device of Embodiment 5 is operated;

FIG. 35 is a graph showing a luminance vs current efficiencycharacteristic when a light-emitting device of Embodiment 5 is operated;and

FIG. 36 is a graph showing an emission spectrum obtained when alight-emitting device of Embodiment 5 is operated.

BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, one mode of the present invention will be described.However, the present invention can be carried out in many differentmodes, and it is easily understood by those skilled in the art thatmodes and details thereof can be modified in various ways withoutdeparting from the spirit and the scope of the present invention.Therefore, the present invention is not understood as being limited tothe description of this mode.

Embodiment Mode 1

Organometallic complexes represented by structural formulas (8) to (34)are given as one mode of the present invention. However, the presentinvention is not limited to the descriptions here, and an organometalliccomplex including a structure represented by any one of general formulas(1), (3), (5), (7), (9), and (11), or an organometallic complexrepresented by any one of general formulas (2), (4), (6), (8), (10),(12), and (13) may be used.

The organometallic complexes of the present invention described aboveemit phosphorescence. Therefore, a light-emitting element having highinternal quantum efficiency and high light-emitting efficiency can bemanufactured by using the organometallic complex of the presentinvention as a light-emitting substance. Also, the organometalliccomplexes of the present invention described above can be synthesizedwith high yield. Therefore, a light-emitting element having low cost ofraw materials can be manufactured by using the organometallic complex ofthe present invention.

Embodiment Mode 2

Hereinafter, a mode of synthesis of an organometallic complex of thepresent invention will be described. Note that the organometalliccomplex of the present invention is not limited to only anorganometallic complex obtained by a synthesis method explained in thismode, and an organometallic complex including a structure represented byany one of general formulas (1), (3), (5), (7), (9), and (11), or anorganometallic complex represented by any one of general formulas (2),(4), (6), (8), (10), (12), and (13) may be used.

[Organometallic Complexes Represented by Structural Formulas (8) to(25)]

An organometallic complex of the present invention represented by anyone of structural formulas (8) to (25) is obtained by a synthesis methodas represented by following synthesis schemes (a-1) to (a-3). First,α-diketone and 1,2-cyclohexanediamine are dehydrated and condensed, andthereafter, dehydrogenated using iron chloride (III) or the like, andaccordingly, a ligand including a skeleton of tetrahydroquinoxaline issynthesized as shown in the synthesis scheme (a-1). Thereafter, thesynthesized ligand is mixed with iridium(III) chloride hydrochloridehydrate and coordinated with iridium, and a dinuclear complex issynthesized as represented by the synthesis scheme (a-2). Furthermore,as represented by the synthesis scheme (a-3), the dinuclear complexwhich is synthesized previously and a monoanionic ligand such asacetylacetone or pocoline acid are reacted, and the monoanionic ligandis coordinated with iridium; accordingly, the organometallic complex ofthe present invention can be obtained.

In the synthesis schemes (a-1) to (a-3), each of R⁴⁹ and R⁵⁰ representsany one of hydrogen, a methyl group, a fluoro group, —CF₃, a methoxygroup, and a phenyl group. L represents any one of acetylacetone,picolone acid, and tetrapyrazolato boronate.

A synthesis method of the organometallic complex of the presentinvention is not limited to the method represented by the synthesisschemes (a-1) to (a-3). However, as in the synthesis method of thismode, by applying a synthesis method including a step in which a ligandis obtained by using 1,2-cyclohexanediamine as a raw material, theorganometallic complex of the present invention can be obtained withhigh yield. This is especially because the yield in synthesizing theligand represented by the synthesis scheme (a-1) becomes high by using1,2-cyclohexanediamine. Here, 1,2-cyclohexanediamine may be either a cisform or a trans form. Alternatively, it may be 1,2-cyclohexanediaminewhich has optical activity, or 1,2-cyclohexanediamine which does nothave optical activity.

In the synthesis scheme (a-1), R⁴⁹ and R⁵⁰ use α-diketone represented byany one of an ethyl group, an isopropyl group, a sec-butyl group, and anethoxy group as a raw material, and accordingly, other organometalliccomplexes of the present invention different from the organometalliccomplexes represented by the structural formulas (8) to (25) can beobtained. Also, by using a salt containing platinum such as tetrachloroplatinum potassium instead of iridium(III) chloride hydrochloridehydrate, an organometallic complex of the present invention containingplatinum as its central metal can be obtained. Also, by using a ligandsuch as dimethyl malonate, salicyl aldehyde, or salicylidene amineinstead of acetylacetone, picolone acid, and tetrapyrazolato boronate,organometallic complexes of the present invention containing ligands asrepresented by structural formulas (2) and (4) to (6) can also beobtained.

[Organometallic Complexes Represented by Structural Formulas (26) to(30)]

An organometallic complex of the present invention represented by anyone of structural formulas (26) to (30) is obtained by a synthesismethod as represented by following synthesis schemes (b-1) to (b-3). Asshown in the synthesis scheme (b-1), α-diketone and1,2-cyclohexanediamine are dehydrated and condensed, and thereafter,dehydrogenated using iron chloride (III) or the like, and accordingly, aligand including a skeleton of tetrahydroquinoxaline is synthesized.Thereafter, the synthesized ligand is mixed with iridium(III) chloridehydrochloride hydrate and coordinated with iridium as represented by thesynthesis scheme (b-2). As represented by the synthesis scheme (b-3), amonoanionic ligand is coordinated with iridium, and a dinuclear complexis synthesized. Furthermore, as represented by the synthesis scheme(b-3), the dinuclear complex which is synthesized previously and amonoanionic ligand, such as acetylacetone or pocoline acid are reacted,and the monoanionic ligand is coordinated with iridium; accordingly, theorganometallic complex of the present invention can be obtained.

In the synthesis schemes (b-1) to (b-3), each of R⁵¹ to R⁵⁴ representsany one of a methyl group, a fluoro group, —CF₃, a methoxy group, and aphenyl group. L represents acetylacetone. Note that α-diketone which isused for a reaction in the synthesis scheme (b-1) can be obtained by areaction of Grignard reagent of benzene, of which the third position andthe fifth position are substituted by any one of a methyl group, afluoro group, —CF₃, a methoxy group and a phenyl group, with1,4-dimethylpiperazine-2,3-dione.

A synthesis method of the organometallic complex of the presentinvention is not limited to the method represented by the synthesisschemes (b-1) to (b-3). However, as in the synthesis method of thismode, by applying a synthesis method including a step in which a ligandis obtained by using 1,2-cyclohexanediamine as a raw material, theorganometallic complex of the present invention can be obtained withhigh yield. This is especially because the yield in synthesizing theligand represented by the synthesis scheme (b-1) becomes high by using1,2-cyclohexanediamine. Here, 1,2-cyclohexanediamine may be either a cisform or a trans form. Alternatively, it may be 1,2-cyclohexanediaminewhich has optical activity or 1,2-cyclohexanediamine which does not haveoptical activity.

In the synthesis scheme (b-1), each of R⁵¹ to R⁵⁴ uses α-diketonerepresented by any one of an ethyl group, an isopropyl group, asec-butyl group, or an ethoxy group as a raw material, and accordingly,other organometallic complexes of the present invention different fromthe organometallic complexes represented by the structural formulas (26)to (30) can be obtained. Also, by using salt containing platinum such astetrachloro platinum potassium instead of iridium(III) chloridehydrochloride hydrate, an organometallic complex of the presentinvention containing platinum as its central metal can be obtained.Also, by using a ligand such as picoline acid, dimethyl malonate,salicyl aldehyde, salicylidene amine, or tetrapyrazolato boronateinstead of acetylacetone, an organometallic complexes of the presentinvention containing ligands as represented by structural formulas (2)to (7) can also be obtained.

[Organometallic Complexes Represented by Structural Formulas (31) to(34)]

An organometallic complex of the present invention represented by anyone of structural formulas (31) to (34) is obtained by a synthesismethod as represented by following synthesis schemes (c-1) to (c-3). Asshown in the synthesis scheme (c-1), α-diketone and1,2-cyclohexanediamine are dehydrated and condensed, and thereafter,dehydrogenated using iron chloride (III) or the like, and accordingly, aligand including a skeleton of tetrahydroquinoxaline is synthesized.Thereafter, the synthesized ligand is mixed with iridium(III) chloridehydrochloride hydrate and coordinated with iridium as represented by thesynthesis scheme (c-2). As represented by the synthesis scheme (c-3), amonoanionic ligand is coordinated with irridium, and a dinuclear complexis synthesized. Furthermore, as represented by the synthesis scheme(c-3), the dinuclear complex which is synthesized previously and amonoanionic ligand such as acetylacetone or pocoline acid are reacted,and the monoanionic ligand is coordinated with iridium; accordingly, theorganometallic complex of the present invention can be obtained.

Here, in the synthesis schemes (c-1) to (c-3), each of R⁵⁵ to R⁶⁰represents any one of a methyl group, a fluoro group, —CF₃, a methoxygroup, and a phenyl group. L represents acetylacetone. Note thatα-diketone which is used for a reaction in the synthesis scheme (c-1)can be obtained by a reaction of Grignard reagent of benzene, in whichthe third, fourth, and fifth positions are substituted by a methylgroup, a fluoro group, —CF₃, and a methoxy group, with1,4-dimethylpiperazine-2,3-dione.

A synthesis method of the organometallic complex of the presentinvention is not limited to the method represented by the synthesisschemes (c-1) to (c-3). However, as in the synthesis method of thismode, by applying the synthesis method including a step in which aligand is obtained by using 1,2-cyclohexanediamine as a raw material,the organometallic complex of the present invention can be obtained withhigh yield. This is especially because the yield in synthesizing theligand represented by the synthesis scheme (c-1) becomes high by using1,2-cyclohexanediamine. Here, 1,2-cyclohexanediamine may be either a cisform or a trans form. Alternatively, it may be 1,2-cyclohexanediaminewhich has optical activity or 1,2-cyclohexanediamine which does not haveoptical activity.

In the synthesis scheme (c-1), each of R⁵⁵ to R⁶⁰ uses α-diketonerepresented by any one of an ethyl group, an isopropyl group, asec-butyl group, and an ethoxy group as a raw material, and accordingly,other organometallic complexes of the present invention different fromthe organometallic complexes represented by the structural formulas (31)to (34) can be obtained. Also, by using salt containing platinum such aspotassium tetrachloro platinate instead of iridium(III) chloridehydrochloride hydrate, an organometallic complex of the presentinvention containing platinum as its central metal can be obtained.Also, by using a ligand such as picoline acid, dimethyl malonate,salicyl aldehyde, salicylidene amine, or tetrapyrazolato bolonateinstead of acetylacetone, organometallic complexes of the presentinvention containing ligands as represented by structural formulas (2)to (7) can be obtained.

Embodiment Mode 3

In this embodiment mode, a mode of a light-emitting element using theorganometallic complex according to Embodiment Modes 1 and 2 will bedescribed with reference to FIG. 1.

FIG. 1 shows a light-emitting element including a light-emitting layer113 between a first electrode 101 and a second electrode 102. Thelight-emitting layer 113 contains an organometallic complex including astructure represented by any one of general formulas (1), (3), (5), (7),(9) and (11), or an organometallic complex represented by any one ofgeneral formulas (2), (4), (6), (8), (10), (12) and (13).

In addition to the light-emitting layer 113, a hole injecting layer 111,a hole transporting layer 112, an electron transporting layer 114, anelectron injecting layer 115, a blocking layer 121, and the like areprovided between the first electrode 101 and the second electrode 102.These layers are stacked so that holes are injected from the firstelectrode 101 and electrons are injected from the second electrode 102,when voltage is applied to make electric potential of the firstelectrode 101 higher than that of the second electrode 102.

In such a light-emitting element, holes injected from the firstelectrode 101 and electrons injected from the second electrode 102 arerecombined in the light-emitting layer 113, and the organometalliccomplex becomes an excited state. The excited organometallic complex ofthe present invention emits light in returning to a ground state. Asdescribed above, the organometallic complex of the present inventionfunctions as a light-emitting substance.

Here, the light-emitting layer 113 is a layer containing theorganometallic complex of the present invention. The light-emittinglayer 113 may be a layer formed by using only the organometallic complexof the present invention; however, in a case where a concentrationquenching phenomenon is generated, the light-emitting layer 113 ispreferably a layer in which a light-emitting substance is mixed to bedispersed in a layer formed by using a substance including a largerenergy gap than that of a light-emitting substance. The organometalliccomplex of the present invention is dispersed and contained in thelight-emitting layer 113, and accordingly, an optical quenching due tothe concentration, that is to say a concentration quenching phenomenon,can be prevented. Here, the energy gap indicates an energy gap between aLUMO level and a HOMO level.

A material which is used for making the organometallic complex of thepresent invention in a dispersed state is not particularly limited;however, in addition to a compound including a skeleton of aryl aminesuch as 2,3-bis(4-diphenylaminophenyl)quinoxaline (abbreviation: TPAQn)or 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation NPB), acarbazole derivative such as 4,4′-di(N-carbazolyl)biphenyl(abbreviation: CBP) or 4,4′,4″-tri(N-carbazolyl)triphenylamine(abbreviation: TCTA); a metal complex such asbis[2-(2-hydroxyphenyl)pyridinato]zinc (abbreviation: Znpp₂) orbis[2-(2-hydroxyphenyl)benzoxazolato]zinc (abbreviation: Zn(BOX)₂), orthe like is preferably used. One or two or more of these materials areselected to be mixed so that the organometallic complex of the presentinvention becomes a dispersed state. As described above, the layercontaining a plurality of compounds can be formed by a co-evaporationmethod. Here, the co-evaporation method is defined to an evaporationmethod by which respective raw materials are vaporized from a pluralityof evaporation sources provided in one processing chamber, and thevaporized raw materials are mixed in a gaseous state to be depositedover a processed substance.

The first electrode 101 and the second electrode 102 are notparticularly limited. In addition to indium tin oxide (ITO), indium tinoxide containing silicon oxide, or indium oxide containing 2 to 20 wt %of zinc oxide, gold (Au); platinum (Pt); nickel (Ni); tungsten (W);chromium (Cr); molybdenum (Mo); iron (Fe); cobalt (Co); copper (Cu);palladium (Pd); and the like can be used. Also, in addition to aluminum,alloy of magnesium and silver; alloy of aluminum and lithium; or thelike can also be used for forming the first electrode 101. Further, aforming method of the first electrode 101 and the second electrode 102is not particularly limited. For example, a sputtering method, anevaporation method, or the like can be used. In order to take out lightemission to the outside, one or both of the first electrode 101 and thesecond electrode 102 is/are preferably formed by using indium tin oxideor the like, or by depositing silver, aluminum or the like to have athickness of several nanometers to several tens nanometers.

The hole transporting layer 112 may also be provided between the firstelectrode 101 and the light-emitting layer 113, as shown in FIG. 1.Here, the hole transporting layer refers to a layer having a function oftransporting holes injected from the first electrode 101 to thelight-emitting layer 113. As described above, by providing the holetransporting layer 112, a distance between the first electrode 101 andthe light-emitting layer 113 can be larger; accordingly, opticalquenching due to metal contained in the first electrode 101 can beprevented. The hole transporting layer is preferably formed by using amaterial having a high hole transporting property, especially, amaterial having hole mobility of 1×10⁻⁶ cm²/Vs or more. Note that amaterial having a high hole transporting property refers to a materialhaving higher mobility of holes than that of electrons and having aratio value of hole mobility to electron mobility (=holemobility/electron mobility) of more than 100. As a specific example of amaterial which can be used for forming the hole transporting layer 112,4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB),4,4′-bis[N-(3-methylphenyl)-N-phenylamino]biphenyl (abbreviation: TPD),4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA),4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine(abbreviation: MTDATA), 4,4′-bis{N-[4-(N,N-di-m-tolylamino)phenyl]-N-phenylamino}biphenyl (abbreviation:DNTPD), 1,3,5-tris[N,N-di(m-tolyl)amino]benzene (abbreviation: m-MTDAB),4,4′,4″-tri(N-carbazolyl)triphenylamine (abbreviation: TCTA),phthalocyanine (abbreviation: H₂Pc), copper phthalocyanine(abbreviation: CuPc), vanadylphthalocyanine (abbreviation: VOPc), or thelike can be given. Also, the hole transporting layer 112 can be formedto have a multilayer structure formed by stacking two or more of layersformed using the above materials.

The electron transporting layer 114 may also be provided between thesecond electrode 102 and the light-emitting layer 113, as shown inFIG. 1. Here, the electron transporting layer refers to a layer having afunction of transporting electrons injected from the second electrode102 to the light-emitting layer 113. As described above, by providingthe electron transporting layer 114, a distance between the secondelectrode 102 and the light-emitting layer 113 can be larger;accordingly, optical quenching due to metal contained in the secondelectrode 102 can be prevented. The electron transporting layer ispreferably formed using a material having a high electron transportingproperty, especially, a material having electron mobility of 1×10⁻⁶cm²/Vs or higher. Note that a material having a high electrontransporting property refers to a material having higher mobility ofelectrons than that of holes and having a ratio value of electronmobility to hole mobility (=electron mobility/hole mobility) of morethan 100. As a specific example of a material for forming the electrontransporting layer 114, in addition to a metal complex such astris(8-quinolinolato)aluminum (abbreviation: Alq₃),tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq₃),bis(10-hydroxybenzo[h]-quinolinato)berylium (abbreviation: BeBq₂),bis(2-methyl-8-quinolinolato)-4-phenylphenolato-aluminum (abbreviation:BAlq), bis[2-(2-hydroxyphenyl)benzoxazolato]zinc (abbreviation:Zn(BOX)₂), bis[2-(2-hydroxyphenyl)benzothiazolato]zinc (abbreviation:Zn(BTZ)₂), 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole(abbreviation: PBD),1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene(abbreviation: OXD-7),3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole(abbreviation: TAZ),3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole(abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen),bathocuproin (abbreviation: BCP), 4,4-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), or the like can be given. Also, theelectron transporting layer 114 can be formed to have a multilayerstructure formed by stacking two or more of layers formed using theabove materials.

In addition to the above materials, each of the hole transporting layer112 and the electron transporting layer 114 may be formed using abipolar substance. A bipolar substance refers to a following substance:when carrier mobility of either electrons or holes is compared withother carrier mobility, a value of a ratio of one carrier mobility tothe other carrier mobility is 100 or less, preferably 10 or less. As thebipolar substance, for example, TPAQn,2,3-bis{4-[N-(1-naphthyl)-N-phenylamino]phenyl}-dibenzo[f,h]quinoxaline(abbreviation: NPADiBzQn), and the like can be given. It is especiallypreferable to use a substance of which hole and electron mobility areeach 1×10⁻⁶ cm²/Vs or more among the bipolar substances. Also, the holetransporting layer 112 and the electron transporting layer 114 may beformed using the same bipolar substance.

Furthermore, the hole injecting layer 111 may be provided between thefirst electrode 101 and the hole transporting layer 112, as shown inFIG. 1. The hole injecting layer 111 refers to a layer having a functionof assisting holes to be injected from the first electrode 101 to thehole transporting layer 112. By providing the hole injecting layer 111,a difference in ionization potential between the first electrode 101 andthe hole transporting layer 112 is relieved, and holes are easilyinjected. The hole injecting layer 111 is preferably formed by amaterial having smaller ionization potential than that of a materialwhich forms the hole transporting layer 112 and larger ionizationpotential than that of a material which forms the first electrode 101,or a material having an energy band which bends when the material isprovided as a thin film having a thickness of 1 to 2 nm between the holetransporting layer 112 and the first electrode 101. As a specificexample of a material which can be used for forming the hole injectinglayer 111, a phthalocyanine derivative such as phthalocyanine(abbreviation: H₂Pc) or copper phthalocyanine (CuPc); a high molecularcompound such as poly(ethylenedioxythiophene)/poly(styrenesulfonic acid)solution (PEDOT/PSS); or the like can be given. In other words, the holeinjecting layer 111 can be formed by selecting a material so thationization potential of the hole injecting layer 111 is relativelysmaller than that of the hole transporting layer 112. Further, in a casewhere the hole injecting layer 111 is provided, the first electrode 101is preferably formed using a material having a high work function, suchas indium tin oxide.

The electron injecting layer 115 may be provided between the secondelectrode 102 and the electron transporting layer 114, as shown inFIG. 1. Here, the electron injecting layer 115 refers to a layer havinga function of assisting electrons to be injected from the secondelectrode 102 to the electron transporting layer 114. By providing theelectron injecting layer 115, a difference in electron affinity betweenthe second electrode 102 and the electron transporting layer 114 can berelieved, and electrons are easily injected. The electron injectinglayer 115 is preferably formed using a material having larger electronaffinity than that of a material which forms the electron transportinglayer 114 and smaller electron affinity than that of a material whichforms the second electrode 102, or a material having an energy bandwhich bends when the material is provided as a thin film of having athickness of 1 to 2 nm between the electron transporting layer 114 andthe second electrode 102. As a specific example of a material which canbe used for forming the electron injecting layer 115, an inorganicmaterial such as alkali metal, alkaline earth metal, fluoride of alkalimetal, fluoride of alkaline earth metal, oxide of alkali metal, or oxideof alkaline earth metal are given. In addition to the inorganicmaterial, a material which can be used for forming the electrontransporting layer 114 such as BPhen, BCP, p-EtTAZ, TAZ, or BzOs canalso be used as a material for forming the electron transporting layer114 by selecting a material of which electron affinity is larger thanthat of a material for forming the electron transporting layer 114 amongthese materials. In other words, the electron injecting layer 115 can beformed by selecting a material so that electron affinity of the electroninjecting layer 115 is relatively larger than that of the electrontransporting layer 114. Further, in a case where the electron injectinglayer 115 is provided, the first electrode 101 is preferably formedusing a material having a low work function, such as aluminum.

As for the above light-emitting element of the present invention, eachof the hole injecting layer 111, the hole transporting layer 112, thelight-emitting layer 113, the electron transporting layer 114, and theelectron injecting layer 115 may be formed by any one of an evaporationmethod, an ink jet method, a coating method, and the like. Also, thefirst electrode 101 or the second electrode 102 may be formed by any oneof a sputtering method, an evaporation method, and the like.

A hole generating layer may also be provided instead of the holeinjecting layer 111, or an electron generating layer may be providedinstead of the electron injecting layer 115. Providing the holegenerating layer or the electron generating layer makes it possible tomanufacture a light-emitting element in which voltage is scarcelyincreased depending on a thickness of the layer.

Here, the hole generating layer refers to a layer which generates holes.The hole generating layer can be formed by mixing at least one materialselected from materials having higher mobility of holes than that ofelectrons and a material showing an electron accepting property withrespect to a material having higher mobility of holes than that ofelectrons, or mixing at least one material selected from bipolarsubstances and a material showing an electron accepting property withrespect to the bipolar substance. Here, as a material having highermobility of holes than that of electrons, materials similar to thematerials which can be used for forming the hole transporting layer 112can be used. As the bipolar substance, the above material such as TPAQn,can be used. In particular, a material having a skeleton oftriphenylamine is used among the materials having higher mobility ofholes than that of electrons and the bipolar substances. Holes areeasily generated by using the material having a skeleton oftriphenylamine. Also, as the material showing an electron acceptingproperty, metal oxide such as molybdenum oxide, vanadium oxide,ruthenium oxide, or rhenium oxide is preferably used.

The electron generating layer refers to a layer which generateselectrons. The electron generating layer can be formed by mixing amaterial having higher mobility of electrons than that of holes and amaterial showing an electron donating property with respect to amaterial having higher mobility of electrons than that of holes, ormixing at least one material selected from bipolar substances and amaterial showing an electron donating property with respect to thebipolar substance. Here, as a material having higher mobility ofelectrons than that of holes, materials similar to the materials whichcan be used for forming the electron transporting layer 114 can be used.As the bipolar substance, the above mentioned bipolar material such asTPAQn can be used. As a material showing an electron donating property,a material selected from alkali metal and alkaline earth metal,specifically, lithium (Li), calcium (Ca), sodium (Na), kalium (Ka),magnesium (Mg), or the like can be used. At least one material selectedfrom alkali metal oxide, alkaline earth metal oxide, alkali metalnitride, alkaline earth metal nitride or the like, specifically, lithiumoxide (Li₂O), calcium oxide (CaO), sodium oxide (Na₂O), kalium oxide(K₂O), magnesium oxide (MgO), or the like can be used as a materialshowing an electron donating property. Also, at least one materialselected from alkali metal fluoride and alkaline earth metal fluoride,specifically, lithium fluoride (LiF), cesium fluoride (CsF), calciumfluoride (CaF₂), or the like can be used as a material showing anelectron donating property. Also, at least one material selected fromalkali metal nitride and alkaline earth metal nitride, specifically,calcium nitride, magnesium nitride, or the like can be used as amaterial showing an electron donating property.

Furthermore, a blocking layer may also be provided between thelight-emitting layer 113 and the hole transporting layer 112, or betweenthe light-emitting layer 113 and the electron transporting layer 114.The blocking layer refers to a layer having a function of preventingholes injected from the first electrode 101 or electrons injected fromthe second electrode 102 from going through the light-emitting layer toenter the other electrode, or a function of preventing excited energygenerated in the light-emitting layer from moving from thelight-emitting layer to the other layer, in addition to a function oftransporting holes or electrons to the light-emitting layer 113. Asshown in FIG. 1, the blocking layer 121 which is provided between thelight-emitting layer 113 and the electron transporting layer 114 and hasa function of preventing holes from going through is specificallyreferred to as a hole blocking layer. Providing the blocking layer makesit possible to suppress a decrease in recombination efficiency due tocarriers that go through and increase light-emitting efficiency. Inaddition, providing the blocking layer makes it possible to decreaselight emission by a substance different from a light-emitting substance,for example, a material or the like which forms the electrontransporting layer which emits light due to a transport of excitedenergy despite its intention.

In the light-emitting element of the present invention as describedabove, it is optional whether or not layers different from thelight-emitting layer, specifically, the hole injecting layer, the holetransporting layer, the electron transporting layer, the electroninjecting layer, and the like are provided, and practitioners of thepresent invention may appropriately select. However, in a case where thehole transporting layer and the electron transporting layer areprovided, effect to decrease optical quenching due to metal contained inthe electrode, the hole injecting layer, the electron injecting layer,or the like is obtained. Also, by providing the electron injectinglayer, the hole injecting layer, or the like, effect to inject electronsor holes from the electrode efficiently is obtained.

The above described light-emitting element of the present invention usesthe organometallic complex of the present invention, for example, thestructural formulas of which are listed in Embodiment Mode 1, as alight-emitting substance; therefore, internal quantum efficiency ishigh, light-emitting efficiency, specifically, luminance for unitvoltage or luminance for unit current density is favorable. Also, in acase where the organometallic complex of the present invention iscontained in the light-emitting element of the present invention as alight-emitting substance, effect to reduce cost of raw materials usedfor manufacturing the light-emitting element can be obtained. This isbecause the organometallic complex of the present invention can besynthesized with high yield as described in Embodiment Mode 2, in otherwords, an organometallic complex with reduced manufacturing cost can beobtained.

Embodiment Mode 4

A light-emitting element of the present invention in which anorganometallic complex of the present invention is used as alight-emitting substance can emit light efficiently; therefore, alight-emitting device in which the light-emitting element of the presentinvention is used as a pixel can be operated with low power consumption.This is because, as described in Embodiment Mode 3, the light-emittingelement of the present invention has favorable luminance for unitvoltage or favorable luminance for unit current density; accordingly,electric power (=current×voltage) which is necessary for light emissionof specific luminance can be decreased by using the light-emittingelement of the present invention as a pixel. Also, the light-emittingdevice of the present invention, in which a light-emitting elementmanufactured at low cost by using the organometallic complex of thepresent invention, is manufactured at low cost and is inexpensive. Inthis embodiment mode, a circuit structure and a driving method of alight-emitting device having a display function will be described withreference to FIGS. 2, 3, 4 and 5.

FIG. 2 is a schematic top view of a light-emitting device to which thepresent invention is applied (a light-emitting device according to thisembodiment mode). In FIG. 2, a pixel portion 6511, a source signal linedriver circuit 6512, a writing gate signal line driver circuit 6513, andan erasing gate signal line driver circuit 6514 are provided over asubstrate 6500. Each of the source signal line driver circuit 6512, thewriting gate signal line driver circuit 6513, and the erasing gatesignal line driver circuit 6514 is connected to an FPC (flexible printedcircuit) 6503 which is an external input terminal through wirings. Eachof the source signal line driver circuit 6512, the writing gate signalline driver circuit 6513, and the erasing gate signal line drivercircuit 6514 receives a video signal, a clock signal, a start signal, areset signal, or the like from the FPC 6503. Also, a printed wiringboard (PWB) 6504 is attached to the FPC 6503. Note that the drivercircuit portion is not necessarily provided over the same substrate asthe pixel portion 6511 as described above. For example, the drivercircuit portion may be provided outside the substrate by using a TCP orthe like where an IC chip is mounted over an FPC having a wiringpattern.

In the pixel portion 6511, a plurality of source signal lines extendingin columns are aligned in rows. Current supply lines are aligned inrows. A plurality of gate signal lines extending in rows are aligned incolumns in the pixel portion 6511. In addition, a plurality of sets ofcircuits each including a light-emitting element are aligned in thepixel portion 6511.

FIG. 3 is a diagram showing a circuit for operating one pixel. Thecircuit shown in FIG. 3 includes a first transistor 901, a secondtransistor 902 and a light-emitting element 903.

Each of the first transistor 901 and the second transistor 902 is athree-terminal element including a gate electrode, a drain region and asource region, and includes a channel region between the drain regionand the source region. Here, the source region and the drain region areswitched depending on a structure, an operational condition, and thelike of the transistor; therefore, it is difficult to determine whichregion functions as a source region or a drain region. Consequently, inthis embodiment mode, each of regions functioning as a source region ora drain region is denoted as a first electrode of a transistor or asecond electrode of a transistor.

A gate signal line 911 and a writing gate signal line driver circuit 913are provided so as to be electrically connected or disconnected to eachother by a switch 918. The gate signal line 911 and an erasing gatesignal line driver circuit 914 are provided so as to be electricallyconnected or disconnected to each other by a switch 919. A source signalline 912 is provided so as to be electrically connected to either asource signal line driver circuit 915 or a power source 916 by a switch920. A gate of the first transistor 901 is electrically connected to thegate signal line 911. Also, a first electrode of the first transistor iselectrically connected to the source signal line 912, and the secondelectrode is electrically connected to a gate electrode of the secondtransistor 902. A first electrode of the second transistor 902 iselectrically connected to a current supply line 917, and a secondelectrode is electrically connected to one electrode included in thelight-emitting element 903. Note that the switch 918 may be included inthe writing gate signal line driver circuit 913. Also, the switch 919may be included in the erasing gate signal line driver circuit 914.Furthermore, the switch 920 may be included in the source signal linedriver circuit 915.

The arrangement of the transistors, the light-emitting element, and thelike is not particularly limited; however, the arrangement shown in atop view of FIG. 4 can be employed. In FIG. 4, a first electrode of afirst transistor 1001 is connected to a source signal line 1004, and asecond electrode is connected to a gate electrode of a second transistor1002. A first electrode of the second transistor is connected to acurrent supply line 1005, and a second electrode is connected to anelectrode 1006 of a light-emitting element. A part of a gate signal line1003 functions as a gate electrode of the first transistor 1001.

Next, a driving method is described. FIG. 5 is a diagram explaining anoperation of a frame with time passage. In FIG. 5, a horizontaldirection indicates time passage while a longitudinal directionindicates the number of scanning stages of a gate signal line.

When an image is displayed by using the light-emitting device of thepresent invention, a rewriting operation of a screen is carried outrepeatedly during a displaying period. The number of the rewritingoperations is not particularly limited. However, the rewriting operationis preferably performed at least about 60 times a second so that aperson who watches a displayed image does not detect flicker. Here, aperiod of performing the rewriting operation of one image (one frame) isreferred to as one frame period.

As shown in FIG. 5, one frame is divided into four sub-frames 501, 502,503, and 504 including writing periods 501 a, 502 a, 503 a, and 504 a,and holding periods 501 b, 502 b, 503 b, and 504 b. A light-emittingelement to which a signal for emitting light is given is in alight-emitting state in the holding periods. The length ratio of theholding periods in the respective sub-frames satisfies the firstsub-frame 501: the second sub-frame 502: the third sub-frame 503: thefourth sub-frame 504=2³:2²:2¹:2⁰=8:4:2:1. This makes it possible toexhibit 4-bit gray scale. However, the number of bits and the number ofgray scales are not limited to those described here. For example, oneframe may be provided with eight sub-frames so as to achieve 8-bit grayscale.

An operation in one frame is described. First, in the sub-frame 501, awriting operation is sequentially performed in first to last rows.Therefore, the starting time of the writing period is differentdepending on each row. The holding period 501 b sequentially starts fromthe row in which the writing period 501 a is terminated. In the holdingperiod, a light-emitting element to which a signal for emitting light isgiven is in a light-emitting state. The next sub-frame 502 sequentiallystarts from the row in which the holding period 501 b is terminated, anda writing operation is sequentially performed in the first to last rowsin the same manner as the sub-frame 501. Operations as described aboveare repeatedly carried out to the holding period 504 b of the sub-frame504, and an operation in the sub-frame 504 is terminated. Afterterminating the operation in the sub-frame 504, an operation in the nextframe starts. Accordingly, the sum of the light-emitting time in therespective sub-frames corresponds to the light-emitting time of eachlight-emitting element in one frame. By changing the light-emitting timefor each light-emitting element and combining such light-emittingelements variously within one pixel, various display colors withdifferent brightness and different chromaticity can be obtained.

As in the sub-frame 504, when the holding period in the row, in whichthe writing is already terminated and the holding period is startedbefore the writing to the last row is terminated, is intended to beforcibly terminated, an erasing period 504 c is preferably providedafter the holding period 504 b to control the row to be forcibly in anon-light-emitting state. The row in which light emission is forciblystopped does not emit light for a certain period (this period isreferred to as a non-light-emitting period 504 d). Right afterterminating the writing period of the last row, a writing period in anext sub-frame (or a next frame) starts sequentially from a first row.This can prevent the writing period in the sub-frame 504 fromoverlapping with the writing period in the next sub-frame.

Although the sub-frames 501 to 504 are arranged in order from the longerholding period in this mode, they are not necessarily arranged in thisorder. For example, the sub-frames may be arranged in order from theshorter holding period. Alternatively, the longer holding period and theshorter holding period may be arranged randomly. Also, the sub-frame mayfurther be divided into a plurality of frames. That is, the gate signalline may be scanned a plurality of times while the same video signalsare given.

Here, an operation of the circuit shown in FIG. 3 in the writing periodand the erasing period is described.

First, an operation in the writing period is described. In the writingperiod, the gate signal line 911 in the n-th row (n is a natural number)is electrically connected to the writing gate signal line driver circuit913 through the switch 918, and is disconnected to the erasing gatesignal line driver circuit 914. Also, the source signal line 912 iselectrically connected to the source signal line driver circuit throughthe switch 920. Here, a signal is inputted to the gate of the firsttransistor 901 which is connected to the gate signal line 911 in then-th row (n is a natural number), and the first transistor 901 is turnedon. At this time, video signals are inputted to the source signal linesin the first column to the last column concurrently. Further, the videosignals inputted from the source signal lines 912 in the respectivecolumns are independent from each other. The video signals inputted fromthe source signal line 912 are inputted to the gate electrode of thesecond transistor 902 through the first transistor 901 which isconnected to each of the source signal lines. At this time, whether thelight-emitting element 903 emits light or not is determined depending onthe signal inputted to the second transistor 902. For example, in a casewhere the second transistor 902 is a P-channel type, the light-emittingelement 903 emits light by inputting a low level signal to the gateelectrode of the second transistor 902. On the other hand, in a casewhere the second transistor 902 is an N-channel type, the light-emittingelement 903 emits light by inputting a high level signal to the gateelectrode of the second transistor 902.

Next, an operation in the erasing period is described. In the erasingperiod, the gate signal line 911 in the n-th row (n is a natural number)is electrically connected to the erasing gate signal line driver circuit914 through the switch 919, and is disconnected to the writing gatesignal line driver circuit 913. Also, the source signal line 912 iselectrically connected to the power source 916 through the switch 920.Here, a signal is inputted to the gate of the first transistor 901connected to the gate signal line 911 in the n-th row, and the firsttransistor 901 is turned on. At this time, erasing signals are inputtedto the source signal lines from the first to the last columnsconcurrently. The erasing signals inputted from the source signal line912 are inputted to the gate electrode of the second transistor 902through the first transistor 901 which is connected to each of thesource signal lines. At this time, supply of a current to thelight-emitting element 903 from the current supply line 917 is blockedby the signals inputted to the second transistor 902. This makes thelight-emitting element 903 emit no light forcibly. For example, in acase where the second transistor 902 is a P-channel type, thelight-emitting element 903 does not emit light by inputting a high levelsignal to the gate electrode of the second transistor 902. On the otherhand, in a case where the second transistor 902 is an N-channel type,the light-emitting element 903 does not emit light by inputting a lowlevel signal to the gate electrode of the second transistor 902.

Further, in the erasing period, a signal for erasing is inputted to then-th row by the operation described above. However, as described above,the n-th row may also be in the erasing period while another row (m-throw (m is a natural number)) is in the writing period. In this case,since a signal for erasing is necessary to be inputted to the n-th rowand a signal for writing is necessary to be inputted to the m-th row byusing the source signal line in the same column, an operation describedbelow is preferably performed

After the light-emitting element 903 in the n-th row becomes anon-light-emitting state by the above-described operation in the erasingperiod, the gate signal line 911 and the erasing gate signal line drivercircuit 914 are immediately disconnected to each other, while the sourcesignal line 912 is connected to the source signal line driver circuit915 by turning on/off the switch 920. Then, the gate signal line 911 andthe writing gate signal line driver circuit 913 are connected to eachother, while the source signal line and the source signal line drivercircuit 915 are connected to each other. A signal is selectivelyinputted to the signal line in the m-th row from the writing gate signalline driver circuit 913 and the first transistor is turned on, whilesignals for writing are inputted to the source signal lines in the firstto the last columns from the source signal line driver circuit 915. Bythese signals, the light-emitting element in the m-th row emits light oremits no light.

After terminating the writing period in the m-th row as described above,the erasing period in the (n+1)-th row immediately starts. Therefore,the gate signal line 911 and the writing gate signal line driver circuit913 are disconnected to each other, while the source signal line isconnected to the power source 916 by turning on/off the switch 920.Moreover, the gate signal line 911 and the writing gate signal linedriver circuit 913 are disconnected to each other, while the gate signalline 911 is connected to the erasing gate signal line driver circuit914. A signal is selectively inputted to the gate signal line in the(n+1)-th row from the erasing gate signal line driver circuit 914 toinput the signal for turning on the first transistor, while an erasingsignal is inputted thereto from the power source 916. As describedabove, after the erasing period in the (n+1)-th row is terminated, thewriting period in the (m+1)-th row immediately starts. Hereinafter, theerasing period and the writing period may be repeated to the erasingperiod of the last row in the same manner.

Although the writing period in the m-th row is provided between theerasing period in the n-th row and the erasing period in the (n+1)-throw is described in this embodiment mode, the present invention is notlimited thereto. The writing period in the m-th row may be providedbetween the erasing period in the (n−1)-th row and the erasing period inthe n-th row.

Furthermore, in this embodiment mode, in a case where thenon-light-emitting period 504 d is provided as in the sub-frame 504, anoperation of disconnecting the erasing gate signal line driver circuit914 with one gate signal line, while connecting the writing gate signalline driver circuit 913 and another gate signal line is performedrepeatedly. This operation may also be performed in a frame in which anon-light-emitting period is not particularly provided.

Embodiment Mode 5

One mode of a sectional structure of a light-emitting device including alight-emitting element of the present invention will be described withreference to FIGS. 6A to 6C.

In FIGS. 6A to 6C, a portion surrounded by a dashed line is a transistor11 which is provided for driving a light-emitting element 12 of thepresent invention. The light-emitting element 12 is a light-emittingelement of the present invention including a layer 15 in which a layergenerating holes, a layer generating electrons, and a layer containing alight-emitting substance of the present invention are stacked between afirst electrode 13 and a second electrode 14. A drain of the transistor11 and the first electrode 13 are electrically connected to each otherby a wiring 17 penetrating a first interlayer insulating film 16 (16 a,16 b and 16 c). Also, the light-emitting element 12 is separated fromanother light-emitting element provided adjacently by a partition layer18. The light-emitting device of the present invention including such astructure is provided over a substrate 10 in this embodiment mode.

Further, the transistor 11 shown in FIGS. 6A to 6C is a top gate type inwhich a gate electrode is provided on an opposite side of the substratewith a semiconductor layer as a center. However, the structure of thetransistor 11 is not particularly limited, for example, a bottom gatetype may also be used. In a case of a bottom gate type, a structure inwhich a protective film is formed over the semiconductor layer whichforms a channel (a channel protected type) may be used, or a structurein which a part of a semiconductor layer which forms a channel isconcave (a channel etched type) may also be used.

A semiconductor layer included in the transistor 11 may be eithercrystalline or amorphous. It may also be semiamorphos.

The semiamorphous semiconductor has an intermediate structure between anamorphous structure and a crystalline structure (including a singlecrystal structure and a polycrystalline structure), and a thirdcondition that is stable in terms of free energy. The semiamorphoussemiconductor includes a crystalline region having a short-range orderand lattice distortion. A crystal grain with a size of 0.5 to 20 nm isincluded in at least part of the film. Raman spectrum is shifted lowerwavenumbers than 520 cm⁻¹. The diffraction peaks of (111) and (220),which are believed to be derived from Si crystal lattice, are observedin X-ray diffraction. The semiamorphous semiconductor contains hydrogenor halogen of at least 1 atom % or more for terminating dangling bonds.Therefore, the semiamorphous semiconductor is also referred to as amicrocrystalline semiconductor. The semiamorphous semiconductor isformed by glow discharge decomposition (plasma CVD) of SiH₄, Si₂H₆,SiH₂Cl₂, SiHCl₃, SiCl₄, or SiF₄. These gases may also be diluted withH₂, or a mixture of H₂ and one or more of rare gas elements selectedfrom He, Ar, Kr, and Ne. The dilution ratio is set to be in a range of 2to 1000 times. The pressure is set to be in the range of approximately0.1 to 133 Pa. The power frequency is set to be 1 to 120 MHz, preferably13 to 60 MHz. The substrate heating temperature may be set to be 300° C.or less, more preferably 100 to 250° C. As impurity elements containedin the film, each concentration of impurities in atmospheric componentssuch as oxygen, nitrogen, and carbon is preferably set to be 1×10²⁰/cm³or less. In particular, the oxygen concentration is set to be 5×10¹⁹/cm³or less, preferably 1×10¹⁹/cm³ or less.

As a specific example of a crystalline semiconductor layer, asemiconductor layer formed from single-crystal silicon, polycrystallinesilicon, silicon germanium, or the like can be given. The crystallinesemiconductor layer may be formed by laser crystallization. For example,the crystalline semiconductor layer may be formed by crystallizationwith use of a solid phase growth method using nickel or the like.

In a case where a semiconductor layer is formed using an amorphousmaterial, for example, an amorphous silicon, it is preferable that allof the transistor 11 and other transistors (transistors included in acircuit for driving a light-emitting element) be a light-emitting devicehaving circuits including N-channel transistors. In other cases, alight-emitting device having circuits including either N-channeltransistors or P-channel transistors may be used. Moreover, alight-emitting device having circuits including both an N-channeltransistor and a P-channel transistor may also be used.

Furthermore, the first interlayer insulating film 16 may be a multilayer as shown in FIGS. 6A to 6C, or a single layer. Note that 16 a isformed of an inorganic material such as silicon oxide or siliconnitride, 16 b is formed of acrylic or siloxane (note that siloxane is acompound that has a Si—O—Si bond as a main skeleton and also includeshydrogen or an alkyl group such as a methyl group as a substituent), ora material with a self-planarizing property which is capable of beingformed by coating deposition, such as silicon oxide. Moreover, 16 c isformed of a silicon nitride film containing argon (Ar). Materialsincluded in each layer are not particularly limited, and materials whichare not described here may also be used. Alternatively, layers formedusing materials other than these materials may be further combined. Asdescribed above, the first interlayer insulating film 16 may be formedusing both an inorganic material and an organic material, or either aninorganic material or an organic material.

An edge portion of the partition layer 18 preferably has a shape inwhich the radius of curvature is continuously changed. The partitionlayer 18 is formed by using acrylic, siloxane, resist, silicon oxide, orthe like. Further, the partition layer 18 may be formed using any one orboth of an inorganic material and an organic material.

In FIGS. 6A to 6C, only the first interlayer insulating film 16 isprovided between the transistor 11 and the light-emitting element 12;however, a second interlayer insulating film 19 (19 a and 19 b) may alsobe provided in addition to the first interlayer insulating film 16 (16 aand 16 b) as shown in FIG. 6B. In a light-emitting device shown in FIG.6B, the first electrode 13 penetrates the second interlayer insulatingfilm 19 to be connected to the wiring 17.

The second interlayer insulating film 19 may be a multi layer includingthe second interlayer insulating films 19 a and 19 b similarly to thefirst interlayer insulating film 16, or a single layer. The secondinterlayer insulating film 19 a is formed of a material with aself-planarizing property which is capable of being formed byapplication deposition, such as silicon oxide. Moreover, the secondinterlayer insulating film 19 b is formed of a silicon nitride filmcontaining argon (Ar). Materials included in each layer are notparticularly limited, and materials which are not described here mayalso be used. Alternatively, layers formed using materials other thanthese materials may be further combined. As described above, the secondinterlayer insulating film 19 may be formed using both an inorganicmaterial and an organic material, or either an inorganic material or anorganic material.

When the first electrode and the second electrode are both formed usinga material having a light-transmitting property in the light-emittingelement 12, light can be taken out through both the first electrode 13and the second electrode 14 as shown by hollow arrows in FIG. 6A. Whenonly the second electrode 14 is formed using a material having alight-transmitting property, light can be taken out only through thesecond electrode 14 as shown by a hollow arrow in FIG. 6B. In this case,the first electrode 13 is preferably formed using a material having highreflectivity, or a film formed using a material having high reflectivity(reflection film) is preferably provided under the first electrode 13.When only the first electrode 13 is formed using a material having alight-transmitting property, light can be taken out only through thefirst electrode 13 as indicated by a hollow arrow in FIG. 6C. In thiscase, the second electrode 14 is preferably formed using a materialhaving high reflectivity or a reflection film is preferably providedabove the second electrode 14.

Moreover, the light-emitting element 12 may have a structure in whichthe layer 15 is stacked so as to operate when voltage is applied to makeelectric potential of the second electrode 14 higher than that of thefirst electrode 13, or a structure in which the layer 15 is stacked soas to operate when voltage is applied so that the electric potential ofthe second electrode 14 is lower than that of the first electrode 13. Inthe former case, the transistor 11 is an N-channel transistor, and inthe latter case, the transistor 11 is a P-channel transistor.

As described above, in this embodiment mode, an active matrix typelight-emitting device, in which drive of the light-emitting element iscontrolled by the transistor, is described. However, the presentinvention may be applied to a passive type light-emitting device withoutbeing limited to an active matrix type light-emitting device.

FIG. 7 is a perspective view showing a passive type light-emittingdevice to which the present invention is applied. In FIG. 7, anelectrode 1902 and an electrode 1906 are provided between a substrate1901 and a substrate 1907. The electrodes 1902 and 1906 are provided soas to be intersected with each other. Furthermore, a light-emittinglayer 1905 (shown by a dashed line so that the electrode 1902, apartition layer 1904, and the like can be seen) is provided between theelectrode 1902 and the electrode 1906. Further; a hole transportinglayer, an electron transporting layer, and the like may be providedbetween the light-emitting layer 1905 and the electrode 1902, or betweenthe light-emitting layer 1905 and the electrode 1906. An edge portion ofthe electrode 1902 is covered with the partition layer 1904. Also, apassive type light-emitting device can be driven with low powerconsumption by including the light-emitting element of the presentinvention which is operated with low driving voltage.

Embodiment Mode 6

A light-emitting device including the light-emitting element of thepresent invention can be driven with low driving voltage; therefore, anelectronic appliance which uses less power and is economical can beobtained by the present invention. Also, a light-emitting devicemanufactured by using the light-emitting element of the presentinvention needs lower manufacturing cost; therefore, an electronicappliance at low price can be obtained by applying the light-emittingelement of the present invention to a display portion.

Embodiments of electronic appliances of the present invention mountedwith a light-emitting device to which the present invention is applied,is shown in FIGS. 8A to 8C.

FIG. 8A shows a computer according to the present invention, and in thecomputer, the light-emitting device of the present invention, in whichthe light-emitting elements using the organometallic complex describedin Embodiment Modes 1 and 2 as a light-emitting substance are aligned ina matrix form, is included in a display portion 5523. In this manner, byincorporating the light-emitting device including the light-emittingelement containing the organometallic complex of the present inventionas a display portion, a computer can be completed. The computer in FIG.8A includes a main body 5521 to which a hard disk, a CPU, and the likeare mounted, a housing 5522 for holding the display portion 5523, akeyboard 5524, and the like, in addition to the display portion 5523.Such a computer is completed using the organometallic complex of thepresent invention, which is synthesized with high yield; therefore, thecomputer needs low cost of raw materials and is inexpensive. Also, acomputer according to the present invention uses the light-emittingdevice of the present invention which is operated with low powerconsumption as a display portion; therefore, power consumption of adisplay is low, and is economical.

FIG. 8B shows a telephone set according to the present invention, and inthe telephone set, the light-emitting device of the present invention,in which the light-emitting elements using the organometallic complexdescribed in Embodiment Modes 1 and 2 as a light-emitting substance arealigned in a matrix form, is included in a display portion 5551 mountedin a main body 5552. In this manner, by incorporating the light-emittingdevice including a light-emitting element containing the organometalliccomplex of the present invention as a display portion, a telephone setcan be completed. The telephone set in FIG. 8B includes an audio outputportion 5554, an audio input portion 5555, operation switches 5556 and5557, an antenna 5553, and the like, in addition to the display portion5551. In this manner, a telephone set can be completed by incorporatingthe light-emitting device including the light-emitting elementcontaining the organometallic complex of the present invention as adisplay portion. Such a telephone set is completed by using theorganometallic complex of the present invention which is synthesizedwith good yield; therefore, the telephone set needs low cost of rawmaterials and is inexpensive. Also, a telephone set according to thepresent invention uses the light-emitting device of the presentinvention which is operated with low power consumption as a displayportion; therefore, power consumption of a display is low, and iseconomical.

FIG. 8C shows a television set according to the present invention, andin the television set, the light-emitting device of the presentinvention, in which the light-emitting elements using the organometalliccomplex described in Embodiment Modes 1 and 2 as a light-emittingsubstance are aligned in a matrix form, is included in a display portion5531. In this manner, by incorporating the light-emitting deviceincluding a light-emitting element containing the organometallic complexof the present invention as a display portion, a television set can becompleted. The television set in FIG. 8C includes a housing 5532 forholding the display portion 5531, a speaker 5533, and the like, inaddition to the display portion 5531. In this manner, a television setcan be completed by incorporating the light-emitting device includingthe light-emitting element containing the organometallic complex of thepresent invention as a display portion. Such a television set iscompleted by using the organometallic complex of the present invention,which is synthesized with high yield; therefore, the television setneeds low cost of raw materials and is inexpensive. Also, a televisionset according to the present invention uses the light-emitting device ofthe present invention which is operated with low power consumption as adisplay portion; therefore, power consumption of a display is low, andis economical.

The above electronic appliances including the light-emitting device ofthe present invention in a display portion, includes, in addition to thecomputer, telephone set, and the like described in FIGS. 8A to 8C,electronic appliances such as a navigation system, a video, a camera,and the like to which the light-emitting device including thelight-emitting element of the present invention is mounted to a displayportion.

Embodiment 1 Synthesis Example 1

A method for synthesizing(acetylacetonato)bis[2,3-diphenyl-5,6,7,8-tetrahydroquinoxalinate]iridium(III)(abbreviation: Ir(dpqtH)₂(acac)), which is one of the organometalliccomplexes of the present invention and is represented by a structuralformula (8) will be described.

[Step 1: Synthesis of Ligand (Abbreviation: DPQtH)]

First, 5.84 g of benzyl (manufactured by Tokyo Kasei Kogyo Co., Ltd) wasmixed with 3.17 g of trans-1,2-cyclohexanediamine (manufactured by KantoKagaku) by using 150 mL of ethanol as a solvent. Then, the mixedsolution was refluxed for 3 hours at 50° C. After that, the refluxedsolution was cooled to be a room temperature. A deposit was obtained byfiltering the refluxed solution. After that,2,3-diphenyl-4a,5,6,7,8,8a-hexahydroquinoxaline was obtained byrecrystallizing the deposit with ethanol (light yellow crystal, yield:96%). Subsequently, 7.66 g of2,3-diphenyl-4a,5,6,7,8,8a-hexahydroquinoxaline, which was obtained inthe above step, was mixed with 8.62 g of iron chloride (III) by using 80mL of ethanol as a solvent. Then the mixed solution was gently stirredwith heat for 3 hours. After the stirring, a ligand2,3-diphenyl-5,6,7,8-tetrahydroquinoxaline (abbreviation: DPQtH) wasobtained by adding water (milky white powder, yield: 88%). A synthesisscheme (d-1) of Step 1 is shown next.

[Step 2: Synthesis of Binuclear Complex (Abbreviation: [Ir(dpqtH)₂Cl]₂)]

Subsequently, 3.98 g of the ligand DPQtH, which was obtained in theabove step, was mixed with 1.65 g of iridium chloride hydrochloridehydrate (IrCl₃, HCl, H₂O) (manufactured by Sigma-Aldrich Co., Ltd) byusing a mixed solution of 30 mL of 2-ethoxyethanol and 10 mL of water asa solvent to reflux under a nitrogen atmosphere for 18 hours;consequently, [Ir(dpqtH)₂Cl]₂ was obtained (red powder, yield: 98%). Asynthesis scheme of Step 3 (d-2) is shown next.

[Step 3: Synthesis of Organometallic Compound of the Present Invention(Abbreviation: Ir(dpqtH)₂(acac))]

Furthermore, 2.06 g of [Ir(dpqtH)₂Cl]₂ which was obtained in the abovestep, 0.40 mL of acethylacetone, and 1.37 g of sodium carbonate aremixed using 30 mL of 2-ethoxyethanol as a solvent. Then, the mixedsolution was refluxed under a nitrogen atmosphere for 17 hours. Afterthat, a deposit obtained by the reflux was filtered; consequently,orange powder was obtained (yield: 53%). Synthesis scheme of Step 3(d-3) is shown next.

The obtained orange powder was analyzed by nuclear magnetic resonancespectroscopy (¹H-NMR), and a result as described below was obtained. Theobtained product was found to be Ir(dpqtH)₂(acac) which is one of theorganometallic complexes of the present invention and is represented bythe structural formula (8). A chart of ¹H-NMR is shown in FIG. 9.

¹H-NMR. δ(CDCl₃): 7.84 (m, 4H), 7.50 (m, 6H), 6.87 (d, 2H), 6.54 (4H),6.41 (d, 2H), 5.04 (s, 1H), 3.08 (m, 6H), 2.69 (2H), 1.87 (m, 6H), 1.73(2H), 1.67 (s, 6H).

A decomposition temperature T_(d) of the obtained organometalliccompound Ir(dpqtH)₂(acac) was measured byThermo-Gravimetric/Differential Thermal Analyzer (manufactured by SeikoInstrument Inc., TG/DTA 320 type), and the result was T_(d)=332° C. Itwas found that the obtained product showed favorable heat resistance.

Subsequently, an absorption spectrum (an ultraviolet-visible lightspectrophotometer, manufactured by Japan Spectroscopy Corporation, V550type) and an emission spectrum (a fluorescence spectrophotometer,manufactured by Hamamatsu Photonics Corporation, FS 920) ofIr(dpqtH)₂(acac) in dichloromethane solution was measured at a roomtemperature. The result is shown in FIG. 10. In FIG. 10, a horizontalaxis indicates a wavelength (nm) and a vertical axis indicates intensityof absorbance and light emission (arbitrary unit). As shown in FIG. 10,the absorption spectrum of Ir(dpqtH)₂(acac) of the present invention haspeaks at 331 nm, 441 nm, 500 nm, and 550 nm. Also, the light emissionspectrum of Ir(dpqtH)₂(acac) has a peak at 590 nm, and it was an orangelight emission.

Also, gas containing oxygen was injected to a dichloromethane solutioncontaining the obtained Ir(dpqtH)₂(acac), and the light emissionintensity was examined when Ir(dpqtH)₂(acac) dissolved with oxygen wasmade to emit light. Furthermore, argon was injected to a dichloromethanesolution containing the obtained Ir(dpqtH)₂(acac), and the lightemission intensity was examined when Ir(dpqtH)₂(acac) dissolved withargon was made to emit light. As a result, it was found thatIr(dpqtH)₂(acac) shows a tendency that the intensity of light emissionobtained in the state with dissolved argon is higher than that obtainedin the state with dissolved oxygen.

Since this tendency is the same as shown by a phosphorescent substance,it has been confirmed that the light emission derived fromIr(dpqtH)₂(acac) is caused by phosphorescence.

Synthesis Example 2

In this synthesis example, a method for synthesizingbis[2,3-bis(4-fluorophenyl)-5,6,7,8-tetrahydroquinoxalinato](picolinato)iridium(III)(abbreviation; Ir(FdpqtH)₂(pic)) which is one of the organometalliccomplexes of the present invention and is represented by a structuralformula (16) will be described.

[Step 1: Synthesis of Ligand (HfdpqtH)]

First, 12.07 g of 4,4′-difluorobenzil (manufactured by Tokyo Kasei KogyoCo., Ltd) was mixed with 5.60 g of trans-1,2-cyclohexanediamine(manufactured by Kanto Kasei Co., Ltd) by using 300 mL of ethanol as asolvent, and then the mixed solution was refluxed under a nitrogenatmosphere for 3 hours. By leaving a the refluxed solution to be cooledto a room temperature and taking out a deposited crystal by filtration,2,3-bis(4-fluorophenyl)-4a,5,6,7,8,8a-hexahydroquinoxaline was obtained(light yellow plate-like crystal, yield: 94%). Subsequently, 6.90 g of2,3-bis(4-fluorophenyl)-4a,5,6,7,8,8a-hexahydroquinoxaline which wasobtained in the above step was mixed with 6.90 g of iron chloride (III)using 150 mL of ethanol as a solvent to gently stir with heat for 3hours at 50° C. After the stirring, a deposition was caused by addingwater to the stirred solution. A deposit was taken out by filtering andwas washed with ethanol. Then, by recrystallizing the deposit withethanol, a ligand 2,3-bis(4-fluorophenyl)-5,6,7,8-tetrahydroquinoxaline(abbreviation: HfdpqtH) was obtained (milky white powder, yield: 68%).Synthesis scheme of Step 1 (e-1) is shown next.

[Step 2: Synthesis of Binuclear Complex [Ir(FdpqtH)₂Cl]₂]

Subsequently, 4.70 g of the ligand FDPQtH which was obtained in theabove step was mixed with 1.74 g of iridium chloride hydrate (IrCl₃,H₂O) (manufactured by Sigma-Aldrich Co., Ltd) by a mixed solution of 30mL of 2-ethoxyethanol and 10 mL of water as a solvent. Then, the mixedsolution was refluxed under a nitrogen atmosphere for 18 hours. Afterthat, a deposited solid obtained by the reflux was filtered;consequently, a binuclear complex [Ir(FdpqtH)₂Cl]₂ was obtained asyellow orange powder (yield: 93%). Synthetic scheme of Step 2 (e-2) isshown next.

[Step 3: Synthesis of an Organometallic Complex (Ir(FdpqtH)₂(pic)) ofthe Present Invention]

Furthermore, 0.90 g of [Ir(FdpqtH)₂Cl]₂ which was obtained in the abovestep was mixed with 0.51 g of picoline acid (manufactured by Tokyo KaseiKogyo Co., Ltd) by using 20 mL of 2-ethoxy ethanol as a solvent. Then,the mixed solution was refluxed under a nitrogen atmosphere for 20hours. After that, a deposited solid was filtered, and yellow powder wasobtained (yield: 59%). Synthetic scheme of Step 3 (e-3) is shown next.

The obtained orange powder was analyzed by nuclear magnetic resonancespectroscopy (¹H-NMR), and a result as described below was obtained. Theobtained product was found to be Ir(FdpqtH)₂(pic) which is one of theorganometallic complexes of the present invention and is represented bythe structural formula (16). A result of analysis of ¹H-NMR is shownbelow, and a chart of ¹H-NMR is shown in FIGS. 16A and 16B. Note thatFIG. 16B is a chart in which part of FIG. 16A is enlarged in a verticaldirection.

¹H-NMR. δ(CDCl₃): 8.31 (d, 1H), 8.26 (d, 1H), 7.94 (td, 1H), 7.85 (m,2H), 7.68 (m, 2H), 7.53 (m, 1H), 7.31-7.19 (m, 4H), 6.97-6.86 (m, 2H),6.43 (td, 1H), 6.33 (td, 1H), 6.20 (dd, 1H), 5.87 (dd, 1H), 3.25-2.73(m, 5H), 1.91 (m, 2H), 1.52 (m, 9H).

A decomposition temperature T_(d) of the obtained organometallic complexIr(FdpqtH)₂(pic) of the present invention was measured byThermo-Gravimetric/Differential Thermal Analyzer (manufactured by SeikoInstrument Inc., TG/DTA 320 type), and the result was T_(d)=342° C. Itwas found that the obtained product showed favorable heat resistance.

Subsequently, an absorption spectrum (an ultraviolet-visible lightspectrophotometer, manufactured by Japan Spectroscopy Corporation, V550type) and an emission spectrum (a fluorescence spectrophotometer,manufactured by Hamamatsu Photonics Corporation, FS 920) ofIr(FdpqtH)₂(pic) was measured at a room temperature using adichloromethane solution which was degassed. The result is shown in FIG.17. In FIG. 17, a horizontal axis indicates a wavelength (nm) and avertical axis indicates intensity (arbitrary unit). As shown in FIG. 10,the organometallic complex (Ir(FdpqtH)₂(pic)) of the present inventionhas absorption peaks at 302 nm, 351 nm, 425 nm, 460 nm, and 520 nm.Also, the light emission spectrum was yellow green light emission whichhad a light emission peak at 550 nm.

Synthesis Example 3

In this synthesis example, a method for synthesizingbis[2,3-bis(4-fluorophenyl)-5,6,7,8-tetrahydroquinoxalinato][tetrakis(1-pyrazolyl)borato]iridium(III)(abbreviation: Ir(FdpqtH)₂(bpz₄)) which is one of the organometalliccomplexes of the present invention and is represented by a structuralformula (22) will be described.

First, 1.10 g of binuclear complex [Ir(FdpqtH)₂Cl]₂, which was obtainedin Step 2 of Synthesis Example 2, was suspended in 40 mL ofdichloromethane. Next, a solution, in which 0.40 g oftrifluoromethansulfonate silver (abbreviation: Ag(OTf)) is dissolved byusing 40 mL of methanol as a solvent, was dropped to the suspension.Subsequently, stirring was performed at a room temperature for 2 hours,the obtained suspension solution was centrifuged, and a supernantsolution obtained by the centrifugation was divided by decantation to beconcentrated and dried. Furthermore, a solid which was obtained by beingconcentrated and dried was mixed with 0.70 g oftetrakis(1-pyrazolyl)borate potassium salt (manufactured by AcrosOrganic Co.) by using 30 mL of acetonitrile as a solvent. Then, themixed solution was refluxed under a nitrogen atmosphere for 18 hours,and yellow powder was obtained (yellow powder, yield: 38%). Synthesisscheme (f-1) is shown next.

The obtained yellow powder was analyzed by nuclear magnetic resonancespectroscopy (¹H-NMR), and a result as described below was obtained. Theobtained product was found to be Ir(FdpqtH)₂(bpz₄) which is one of theorganometallic complexes of the present invention and is represented bythe structural formula (22). A result of analysis of ¹H-NMR is shownbelow, and a chart of ¹H-NMR is shown in FIGS. 18A and 18B. Note thatFIG. 18B is a chart in which part of FIG. 18A is enlarged in a verticaldirection.

¹H-NMR. δ(ACETONE-d₆): 7.70-7.63 (m, 6H), 7.30-7.10 (m, 8H), 6.92-6.83(m, 2H), 6.41-6.27 (m, 4H), 6.20-6.14 (m, 2H), 6.11-6.00 (m, 4H), 2.89(m, 2H), 1.68-1.47 (m, 14H).

A decomposition temperature T_(d) of the obtained organometallic complexof the present invention Ir(FdpqtH)₂(bpz₄) was measured by TG/DTA, andit was found that T_(d)=346° C. and the obtained product showedfavorable heat resistance.

Subsequently, an absorption spectrum (an ultraviolet-visible lightspectrophotometer, manufactured by Japan Spectroscopy Corporation, V550type) and an emission spectrum (a fluorescence spectrophotometer,manufactured by Hamamatsu Photonics Corporation, FS 920) ofIr(FdpqtH)₂(bpz₄) were measured at a room temperature using adichloromethane solution which was degassed. The result is shown in FIG.19. In FIG. 19, a horizontal axis indicates a wavelength (nm) and avertical axis indicates intensity (arbitrary unit). As shown in FIG. 19,the organometallic complex Ir(FdpqtH)₂(bpz₄) of the present inventionhas absorption peaks at 344 nm, 412 nm, 440 nm, and 475 nm. Also, thelight emission spectrum was orange light emission which had a lightemission peak at 600 nm.

Synthesis Example 4

In this synthesis example, a method for synthesizing(acetylacenato)bis[2,3-bis(4-fluorophenyl)-5,6,7,8-tetrahydroquinoxalinato]iridium(III)(abbreviation: Ir(FdpqtH)₂(acac)) which is one of the organometalliccomplexes of the present invention and is represented by a structuralformula (10) will be described.

2.26 g of the binuclear complex [Ir(FdpqtH)₂Cl]₂ which was obtained inStep 2 of Synthesis Example 2, 0.47 mL of acetylacetone, and 1.62 g ofsodium carbonate were mixed using 30 mL of 2-ethoxyethanol as a solvent.Next, the mixed solution was refluxed under a nitrogen atmosphere for 16hours. After that, a deposited solid by the reflux was filtered;consequently, orange power was obtained (yield: 39%). A synthesis scheme(g-1) is shown next.

The obtained orange power was analyzed by nuclear magnetic resonancespectroscopy (¹H-NMR), and a result as described below was obtained. Theobtained product was found to be Ir(FdpqtH)₂(acac) which is one of theorganometallic complexes of the present invention and is represented bythe structural formula (10). A result of analysis of ¹H-NMR is shownbelow, and a chart of ¹H-NMR is shown in FIGS. 20A and 20B. Note thatFIG. 20B is a chart in which part of FIG. 20A is enlarged in a verticaldirection.

¹H-NMR. δ(CDCl₃): 7.81 (t, 4H), 7.21 (m, 4H), 6.85 (m, 2H), 6.30 (td,2H), 6.03 (dd, 2H), 5.06 (s, 1H), 3.18-2.93 (m, 6H), 2.67-2.58 (m, 2H),1.99-1.77 (m, 8H), 1.68 (s, 6H).

A decomposition temperature T_(d) of the obtained organometallic complexIr(FdpqtH)₂(acac) of the present invention was measured by TG/DTA, andit was found that T_(d)=332° C. and the obtained product showedfavorable heat resistance.

Subsequently, an absorption spectrum (an ultraviolet-visible lightspectrophotometer, manufactured by Japan Spectroscopy Corporation, V550type) and an emission spectrum (a fluorescence spectrophotometer,manufactured by Hamamatsu Photonics Corporation, FS 920) ofIr(FdpqtH)₂(acac) were measured at a room temperature using adichloromethane solution which was degassed. The result is shown in FIG.21. In FIG. 21, a horizontal axis indicates a wavelength (nm) and avertical axis indicates absorption intensity (arbitrary unit). As shownin FIG. 21, the organometallic complex Ir(FdpqtH)₂(acac) of the presentinvention has absorption peaks at 295 nm, 357 nm, 432 nm, 475 nm, and535 nm. Also, the light emission spectrum was yellow light emissionwhich had a light emission peak at 565 nm.

Synthesis Example 5

In synthesis example, this(acetylacenato)[2,3-bis(4-fluorophenyl)-5,6,7,8-tetrahydroquinoxalinato]platinum(II)(abbreviation: Pt(FdpqtH)(acac)) which is one of the organometalliccomplexes of the present invention and is represented by a structuralformula (35) will be described.

First, 2.15 g of the ligand Hfdpqt which was obtained in Step 1 ofSynthesis Example 2 was mixed with 1.11 g of potassium tetrachloroplatinate (K₂[PtCl₄]) by using a mixed solution of 30 mL of2-ethoxyethanol and 10 mL of water. Next, the mixed solution was stirredwith heat at 80° C. under a nitrogen atmosphere for 17 hours. Thesolvent was removed from the stirred solution, the obtained powder waswashed with ethanol, and was dried overnight under reduced pressure.Subsequently, the dried powder, 0.41 mL of acetylacetone, and 1.42 g ofsodium carbonate was mixed with 30 mL of 2-ethoxyethanol solution. Then,the mixed solution was refluxed under a nitrogen atmosphere for 16hours. A deposit obtained by filtering the refluxed solution was washedwith methanol, and was recrystallized by using dichloromethane;consequently, orange powder was obtained. A synthesis scheme (h-1) isshown next.

The obtained orange power was analyzed by nuclear magnetic resonancespectroscopy (¹H-NMR), and a result as described below was obtained. Theobtained product was found to be Pt(FdpqtH)(acac) which is one of theorganometallic complexes of the present invention and is represented bya structural formula (10). A result of analysis of ¹H-NMR is shownbelow, and a chart of ¹H-NMR is shown in FIGS. 22A and 22B. Note thatFIG. 22B is a chart in which part of FIG. 22A is enlarged in a verticaldirection.

¹H-NMR. δ(CDCl₃): 7.24 (m, 2H), 7.24-7.13 (m, 3H), 6.56 (dd, 1H), 6.44(td, 1H), 5.55 (s, 1H), 3.56 (brm, 2H), 3.02 (brm, 2H), 2.04 (s, 3H),1.98 (s, 3H), 1.94 (brm, 4H).

A decomposition temperature T_(d) of the obtained organometallic complexPt(FdpqtH)(acac) of the present invention was measured by TG/DTA, and itwas found that T_(d)=239° C.

Subsequently, an absorption spectrum (an ultraviolet-visible lightspectrophotometer, manufactured by Japan Spectroscopy Corporation, V550type) and an emission spectrum (a fluorescence spectrophotometer,manufactured by Hamamatsu Photonics Corporation, FS 920) ofPt(FdpqtH)(acac) were measured at a room temperature using adichloromethane solution which was degassed. The result is shown in FIG.23. In FIG. 23, the horizontal axis indicates a wavelength (nm) and thevertical axis indicates intensity (arbitrary unit). As shown in FIG. 23,the organometallic complex Pt(FdpqtH)(acac) of the present invention hasabsorption peaks at 324 nm, 357 nm, 389 nm, 439 nm, and 469 nm. Also,the light emission spectrum was orange-red light emission which had alight emission peak at 620 nm.

Embodiment 2

In this embodiment, a method for manufacturing a light-emitting elementusing Ir(dpqtH)₂(acac) synthesized by the method described in SynthesisExample 1 as a light-emitting substance, and an operationalcharacteristic thereof will be described.

As shown in FIG. 11, indium tin oxide containing silicon oxide wasdeposited on a glass substrate 301 by a sputtering method, and a firstelectrode 302 was formed. The first electrode 302 was formed to have athickness of 110 nm. Further, the electrode was formed to be squarehaving a size of 2 mm×2 mm.

Subsequently, the glass substrate 301, on which the first electrode 302was formed, was fixed to a holder provided in a vacuum evaporationapparatus so that a surface where the first electrode faced downward.

Subsequently, the air inside the vacuum evaporation apparatus wasevacuated, and decompressed to be 1×10⁻⁴ Pa, and thereafter, a firstlayer 303 containing NPB and molybdenum oxide was formed on the firstelectrode 302 by a co-evaporation method. In this embodiment, hexavalentmolybdenum oxide (MoO₃) was used as molybdenum oxide. The first layer303 was formed to be 50 nm thick. The molar ratio of NPB to molybdenumoxide was 1:2=NPB:molybdenum oxide. The first layer 303 functions as ahole generating layer when the light-emitting element is operated.

A second layer 304 containing NPB was formed on the first layer 303 byan evaporation method. The second layer 304 was formed to be 10 nmthick. The second layer 304 functions as a hole transporting layer whenthe light-emitting element is operated.

A third layer 305 containing CBP and Ir(dpqtH)₂(acac) was formed on thesecond layer 304 by a co-evaporation method. The third layer 305 wasformed so as to be 30 nm thick and the mass ratio of CBP toIr(dpqtH)₂(acac) was 1:0.025=CBP:Ir(dpqtH)₂(acac)(1:0.014=CBP:Ir(dpqtH)₂(acac), in being converted into the molar ratio).Consequently, Ir(dpqtH)₂(acac) is in such a state in whichIr(dpqtH)₂(acac) is dispersed in the layer containing CBP. The thirdlayer 305 functions as a light-emitting layer when the light-emittingelement is operated.

A fourth layer 306 containing BCP was formed on the third layer 305 byan evaporation method. The fourth layer 306 was formed to be 20 nmthick. The fourth layer 306 functions as a hole blocking layer when thelight-emitting element is operated.

A fifth layer 307 containing Alg₃ was formed on the fourth layer 306 byan evaporation method. The fifth layer 307 was formed to be 30 nm thick.The fifth layer 307 functions as an electron transporting layer when thelight-emitting element is operated.

A sixth layer 308 containing calcium fluoride was formed on the fifthlayer 307 by an evaporation method. The sixth layer 308 was formed to be1 nm thick. The sixth layer 308 functions as an electron injecting layerwhen the light-emitting element is operated.

A second electrode 309 containing aluminum was formed on the sixth layer308. The second electrode 309 was formed to be 200 nm thick.

Current flows when voltage is applied to the light-emitting elementmanufactured as described above so that electric potential of the firstelectrode 302 is higher than that of the second electrode 309. Electronsand holes are recombined in the third layer 305 functioning as alight-emitting layer, and excited energy is generated. The excitedIr(dpqtH)₂(acac) emits light in returning to a ground state.

The light-emitting element was sealed in a globe box under a nitrogenatmosphere without being exposed to the atmospheric air. Thereafter, anoperational characteristic of the light-emitting element was measured.Note that the measurement was carried out at a room temperature (underan atmosphere maintaining 25° C.).

Measurement results are shown in FIGS. 12 to 14. FIG. 12 shows ameasurement result of a current density-luminance characteristic, FIG.13 shows a measurement result of a voltage-luminance characteristic, andFIG. 14 shows a measurement result of a luminance-current efficiencycharacteristic. In FIG. 12, a horizontal axis represents current density(mA/cm²) and a vertical axis represents luminance (cd/m²). In FIG. 13, ahorizontal axis represents voltage (V) and a vertical axis representsluminance (cd/m²). In FIG. 14, a horizontal axis represents luminance(cd/m²) and a vertical axis represents current efficiency (cd/A).According to these results, it was found that current flows with thecurrent density of 2.29 mA/cm² in the light-emitting elementmanufactured in this embodiment when voltage of 8V is applied, and thelight-emitting element emits light with the luminance of 490 cd/m².Further, the current efficiency when the light-emitting element wherelight is emitted with the luminance of 490 cd/m² was 21 cd/A, and it was10% in being converted into external quantum efficiency (the number ofphotons/the number of electrons). Applying the stacked structure asshown in this embodiment makes it possible to obtain favorable lightemission derived from the organometallic complex of the presentinvention.

Also, an emission spectrum of the light-emitting element manufactured inthis embodiment is shown in FIG. 15. In FIG. 15, a horizontal axisrepresents a wavelength (nm) and a vertical axis represents intensity(arbitrary unit). According to FIG. 15, it was found that thelight-emitting element of this embodiment has a peak of an emissionspectrum at 580 nm and emits orange light.

Embodiment 3

In this embodiment, a method for manufacturing a light-emitting elementusing Ir(FdpqtH)₂(pic) synthesized in Synthesis Example 2 as alight-emitting substance and an operational characteristic thereof willbe described with reference to FIGS. 24 and 25 to 28.

As shown in FIG. 24, indium tin oxide containing silicon oxide wasdeposited on a glass substrate 401 by a sputtering method, and a firstelectrode 402 was formed. The first electrode 402 was formed to have athickness of 110 nm.

Subsequently, the glass substrate 401, on which the first electrode 402was formed, was fixed on a holder provided in a vacuum evaporationapparatus so that a surface where the first electrode faced downward.

The pressure inside the vacuum evaporation apparatus was reduced to be1×10⁻⁴ Pa, and thereafter, a first layer 403 containing DNTPD was formedon the first electrode 402. The first layer 403 was formed to be 50 nmthick. The first layer 403 functions as a hole injecting layer when thelight-emitting element is operated.

A second layer 404 containing NPB was formed on the first layer 403 byan evaporation method. The second layer 404 was formed to be 10 nmthick. The second layer 404 functions as a hole transporting layer whenthe light-emitting element is operated.

A third layer 405 containing CBP and Ir(FdpqtH)₂(pic) was formed on thesecond layer 404 by a co-evaporation method. The third layer 405 wasformed so as to be 30 nm thick and the mass ratio of CBP toIr(FdpqtH)₂(pic) was 1:0.05=CBP:Ir(FdpqtH)₂(pic). Consequently,Ir(FdpqtH)₂(pic) is in such a state in which Ir(FdpqtH)₂(pic) iscontained in a layer having CBP as a matrix. The third layer 405functions as a light-emitting layer when the light-emitting element isoperated. In such a case, Ir(FdpqtH)₂(pic) is referred to as a guest,and CBP is referred to as a host.

The fourth layer 406 containing BCP is formed on the third layer 405 byan evaporation method. The fourth layer 406 was formed to be 20 nmthick. The fourth layer 406 functions as an electron transporting layerwhen the light-emitting element is operated.

A fifth layer 407 containing Alq₃ and Li was formed on the fourth layer406 by a co-evaporation method. The fifth layer 407 was formed so as tobe 30 nm thick and mass ratio of Alga to Li was 1:0.01=Alq₃:Li. Thefifth layer 407 functions as an electron injecting layer when thelight-emitting element is operated.

A second electrode 408 containing aluminum was formed on the fifth layer407. The second electrode 408 was formed to be 200 nm thick.

Current flows when voltage is applied to the light-emitting elementmanufactured as described above so that electric potential of the firstelectrode 402 is higher than that of the second electrode 408. Electronsand holes are recombined in the third layer 405 functioning asalight-emitting layer, and excited energy is generated. The excitedIr(FdpqtH)₂(pic) emits light in returning to a ground state.

The light-emitting element was sealed in a globe box under a nitrogenatmosphere without being exposed to the atmospheric air. Thereafter, anoperational characteristic of the light-emitting element was measured.Note that the measurement was carried out at a room temperature (underan atmosphere maintaining 25° C.).

Measurement results are shown in FIGS. 25 to 27. FIG. 25 shows ameasurement result of a current density-luminance characteristic, FIG.26 shows a measurement result of a voltage-luminance characteristic, andFIG. 27 shows a measurement result of a luminance-current efficiencycharacteristic. In FIG. 25, a horizontal axis represents current density(mA/cm²) and a vertical axis represents luminance (cd/m²). In FIG. 26, ahorizontal axis represents voltage (V) and a vertical axis representsluminance (cd/m²). In FIG. 27, a horizontal axis represents luminance(cd/m²) and a vertical axis represents current efficiency (cd/A).According to these results, it was found that the light-emitting elementof this embodiment emits light with the current density of 3.86 mA/cm²and with the luminance of 942 cd/m² when voltage of 9V is applied. Thecurrent efficiency at this time was 24.4 cd/A, and external quantumefficiency was 10.8%, which was high. Furthermore, when thelight-emitting element where light is emitted with the luminance of 20.6cd/m², the external quantum efficiency was 13.7%, which was a maximumvalue.

Light emission spectrum of the light-emitting element manufactured inthis embodiment is shown in FIG. 28. In FIG. 28, a horizontal axisrepresents a wavelength (nm) and a vertical axis represents intensity(arbitrary unit). Furthermore, CIE chromaticity coordinate was x=0.51,and y=0.48, and it was found that the light-emitting element of thisembodiment represented yellow light.

Further, as shown in FIG. 28, the trapezoidal shaped light emissionspectrum (half width=140 nm) which has less change in light emissionintensity in a range of wavelengths of 550 to 650 am can be obtainedfrom the light-emitting element of this embodiment. Therefore, whitelight can be obtained by combining the light-emitting element of thisembodiment with a light-emitting element showing a gentle peak shapedlight emission spectrum which has less change in light emissionintensity in a range of wavelengths of 450 to 550 nm so that the lightemission spectrum is synthesized (for example, these light-emittingelements are made to emit light concurrently). Furthermore, white lightcan be obtained by providing a layer containing a light-emittingsubstance showing a gentle peak shaped light emission spectrum which hasless change in light emission intensity in a range of wavelengths of 450to 550 nm in the light-emitting element of this embodiment, and forminga layer provided between the electrodes so that Ir(FdpqtH)₂(pic) and thelight-emitting substance emit light concurrently.

Embodiment 4

In this embodiment, an operational characteristic of a light-emittingelement using Ir(FdpqtH)₂(bpz₄) synthesized in Synthesis Example 3 as alight-emitting substance will be described with reference to FIGS. 29 to32.

The light-emitting element manufactured in this embodiment is differentfrom the light-emitting element in Embodiment 3, in terms of usingIr(FdpqtH)₂(bpz₄) instead of Ir(FdpqtH)₂(pic); however, structures otherthan that (a substance, thickness, mass ratio, and the like used forforming each layer) are the same as Embodiment 3. Therefore, Embodiment3 is referred to for a manufacturing method and an element composition,and the description is omitted here.

Measurement results of operational characteristics of the manufacturedlight-emitting element are shown in FIGS. 29 to 31. FIG. 29 shows ameasurement result of a current density-luminance characteristic, FIG.30 shows a measurement result of a voltage-luminance characteristic, andFIG. 31 shows a measurement result of a luminance-current efficiencycharacteristic. In FIG. 29, a horizontal axis represents current density(mA/cm²) and a vertical axis represents luminance (cd/m²). In FIG. 30, ahorizontal axis represents voltage (V) and a vertical axis representsluminance (cd/m²). In FIG. 31, a horizontal axis represents luminance(cd/m²) and a vertical axis represents current efficiency (cd/A).According to these results, it was found that the light-emitting elementof this embodiment emits light with the current density of 7.29 mA/cm²and with the luminance of 1050 cd/m² when voltage 9.2V is applied. Thecurrent efficiency at this time was 14.4 cd/A, and external quantumefficiency was 7.76%, which was high. Furthermore, when thelight-emitting element where light is emitted with the luminance of 7.78cd/m², the external quantum efficiency was 11.0%, which was a maximumvalue.

A light emission spectrum of the light-emitting element manufactured inthis embodiment is shown in FIG. 32. In FIG. 32, a horizontal axisrepresents a wavelength (nm) and a vertical axis represents intensity(arbitrary unit). Furthermore, CIE chromaticity coordinate was x=0.54,and y=0.45, and it was found that the light-emitting element of thepresent invention represented yellow-orange light.

Further, as shown in FIG. 32, a gentle peak shaped light emissionspectrum (half width=145 nm) which has less change in light emissionintensity in a range of wavelengths of 550 to 650 nm can be obtainedfrom the light-emitting element of this embodiment. Therefore, whitelight can be obtained by combining the light-emitting element of thisembodiment with a light-emitting element showing a gentle peak shapedlight emission spectrum which has wide peak in a range of wavelengths of450 to 550 nm so that the light emission spectrum is synthesized (forexample, these light-emitting elements are made to emit lightconcurrently). Furthermore, white light can be obtained by providing alayer containing a light-emitting substance showing peak shaped lightemission spectrum which has less change in light emission intensity in arange of wavelengths of 450 to 550 nm in the light-emitting element ofthis embodiment, and forming a layer provided between electrodes so thatIr(FdpqtH)₂(bpz₄) and the light-emitting substance emit lightconcurrently.

Embodiment 5

In this embodiment, a method for manufacturing a light-emitting elementusing Ir(FdpqtH)₂(acac) synthesized in Synthesis Example 4 as alight-emitting substance and an operational characteristic thereof willbe described with reference to FIGS. 24 and 33 to 36.

As shown in FIG. 24, indium tin oxide containing silicon oxide wasdeposited on a glass substrate 401 by a sputtering method, and a firstelectrode 402 was formed. The first electrode 402 was formed to be 110nm thick.

The glass substrate 401 on which the first electrode 402 was formed wasfixed on a holder provided in a vacuum evaporation apparatus so that asurface where the first electrode 402 was formed faced downward.

The pressure in the vacuum evaporation apparatus was reduced to be1×10⁻⁴ Pa, and thereafter, a first layer 403 containing NPB andmolybdenum oxide was formed on the first electrode 402 by aco-evaporation method. In this embodiment, hexavalent molybdenum oxide(MoO₃) was used as molybdenum oxide. The first layer 403 was formed tobe 50 nm thick. The molar ratio of NPB to molybdenum oxide was1:1=NPB:molybdenum oxide. The first layer 403 functions as a holegenerating layer when the light-emitting element is operated.

A second layer 404 containing TCTA was formed on the first layer 403 byan evaporation method. The second layer 404 was formed to be 10 nmthick. The second layer 404 functions as a hole transporting layer whenthe light-emitting element is operated.

A third layer 405 containing CBP and Ir(FdpqtH)₂(acac) was formed on thesecond layer 404 by a co-evaporation method. The third layer 405 wasformed so as to be 30 nm thick, and the mass ratio of CBP toIr(FdpqtH)₂(acac) was 1:0.01=CBP:Ir(FdpqtH)₂(acac). Consequently,Ir(FdpqtH)₂(acac) is in such a state in which Ir(FdpqtH)₂(acac) iscontained in a layer having CBP as a matrix. The third layer 405functions as a light-emitting layer when the light-emitting element isoperated. In such a case, Ir(FdpqtH)₂(acac) is referred to as a guest,and CBP is referred to as a host.

A fourth layer 406 was containing TAZ formed on the third layer 405 byan evaporation method. The fourth layer 406 was formed to be 20 nmthick. The fourth layer 406 functions as an electron transporting layerwhen the light-emitting element is operated.

A fifth layer 407 containing TAZ and Li was formed on the fourth layer406 by a co-evaporation method. The fifth layer 407 is formed to be 30nm thick. Mass ratio of TAZ to Li was set to be 1:0.01=TAZ:Li. The fifthlayer 407 functions as an electron injecting layer when thelight-emitting element is operated.

A second electrode 408 containing aluminum was formed on the fifth layer407. The second electrode 408 was formed to be 200 nm thick.

Current flows when voltage is applied to the light-emitting elementmanufactured as described above so that electric potential of the firstelectrode 402 is higher than that of the second electrode 408. Electronsand holes are recombined in the third layer 405 functioning as alight-emitting layer, and excited energy is generated. The excitedIr(FdpqtH)₂(acac) emits light in returning to a ground state.

The light-emitting element was sealed in a sealing apparatus under anitrogen atmosphere without being exposed to the atmospheric air.Thereafter, an operational characteristic of the light-emitting elementwas measured. Note that the measurement was carried out at a roomtemperature (under an atmosphere maintaining 25° C.).

Measurement results are shown in FIGS. 33 to 35. FIG. 33 shows ameasurement result of a current density-luminance characteristic, FIG.34 shows a measurement result of a voltage-luminance characteristic, andFIG. 35 shows a measurement result of a luminance-current efficiencycharacteristic. In FIG. 33, a horizontal axis represents current density(mA/cm²) and a vertical axis represents luminance (cd/m²). In FIG. 34, ahorizontal axis represents voltage (V) and a vertical axis representsluminance (cd/m²). In FIG. 35, a horizontal axis represents luminance(cd/m²) and a vertical axis represents current efficiency (cd/A).According to these results, it was found that current flows with thecurrent density of 2.47 mA/cm² in the light-emitting element of thisembodiment, and the light-emitting element emits light with theluminance of 915 cd/m² when voltage of 6.4V is applied. The currentefficiency at this time was 37.0 cd/A, and external quantum efficiencywas 13.8%, which was high. Furthermore, when the light-emitting elementwhere light is emitted with the luminance of 38.7 cd/m², the externalquantum efficiency was 15.0%, which was a maximum value.

A light emission spectrum of the light-emitting element manufactured inthis embodiment is shown in FIG. 36. In FIG. 36, a horizontal axisrepresents a wavelength (nm) and a vertical axis represents intensity(arbitrary unit). Furthermore, CIE chromaticity coordinate was x=0.52,and y=0.48, and it was found that the light-emitting element of thepresent invention represented yellow light.

Further, as shown in FIG. 36, a gentle peak shaped light emissionspectrum (half width=100 nm) which has less change in light emissionintensity in a range of wavelengths of 550 to 650 nm can be obtainedfrom the light-emitting element of this embodiment. Therefore, whitelight can be obtained by combining the light-emitting element of thisembodiment with a light-emitting element showing a gentle peak shapedlight emission spectrum which has less change in light emissionintensity in a range of wavelengths of 450 to 550 nm so that the lightemission spectrum is synthesized (for example, these light-emittingelements are made to emit light concurrently). Furthermore, white lightcan be obtained by providing a layer containing a light-emittingsubstance showing a gentle peak shaped light emission spectrum which hasless change in light emission intensity in a range of wavelengths of 450to 550 nm in the light-emitting element of this embodiment, and forminga layer provided between electrodes so that Ir(FdpqtH)₂(acac) and thelight-emitting substance emit light concurrently.

This application is based on Japanese Patent Application serial no.2005-091349 filed in Japan Patent Office on 28, Mar., 2005 and JapanesePatent Application serial no. 2005-324037 filed in Japan Patent Officeon 8, Nov., 2005, the entire contents of which are hereby incorporatedby reference.

1. A light-emitting device comprising: a first electrode; an insulatinglayer covering an end portion of the first electrode; a layer comprisingan organometallic complex over the first electrode and the insulatinglayer; and a second electrode over the layer comprising theorganometallic complex, wherein the organometallic complex comprises astructure represented by a general formula (1),

wherein each of R¹ and R² represents any one of hydrogen, an alkylgroup, a halogen, a trifluoromethyl group, an alkoxy group, and an arylgroup, and wherein M represents an element that belongs to Group 9 orGroup
 10. 2. The light-emitting device according to claim 1, wherein Mis iridium.
 3. The light-emitting device according to claim 1 furthercomprising a transistor electrically connected to the first electrode,wherein the first electrode is provided over the transistor.
 4. Thelight-emitting device according to claim 3, wherein the transistorcomprises: a semiconductor film; and a gate electrode over thesemiconductor film.
 5. An electronic appliance comprising thelight-emitting device according to claim 1, wherein the electronicappliance is one selected from the group consisting of a computer, atelephone set, and a television set.
 6. The light-emitting deviceaccording to claim 1, wherein the organometallic complex is representedby a general formula (2),

wherein L represents a monoanionic ligand, and wherein n=2 when M is anelement that belongs to Group 9, and n=1 when M is an element thatbelongs to Group
 10. 7. A light-emitting device comprising: a firstelectrode; an insulating layer covering an end portion of the firstelectrode; a layer comprising an organometallic complex over the firstelectrode and the insulating layer; and a second electrode over thelayer comprising the organometallic complex, wherein the organometalliccomplex comprises a structure represented by a general formula (5),

wherein each of R⁹ to R¹² represents any one of hydrogen, an alkylgroup, a halogen, a trifluoromethyl group, an alkoxy group, and an arylgroup, and wherein M represents an element that belongs to Group 9 orGroup
 10. 8. The light-emitting device according to claim 7, wherein Mis iridium.
 9. The light-emitting device according to claim 7 furthercomprising a transistor electrically connected to the first electrode,wherein the first electrode is provided over the transistor.
 10. Thelight-emitting device according to claim 9, wherein the transistorcomprises: a semiconductor film; and a gate electrode over thesemiconductor film.
 11. An electronic appliance comprising thelight-emitting device according to claim 7, wherein the electronicappliance is one selected from the group consisting of a computer, atelephone set, and a television set.
 12. The light-emitting deviceaccording to claim 7, wherein the organometallic complex is representedby a general formula (6),

wherein L represents a monoanionic ligand, and wherein n=2 when M is anelement that belongs to Group 9, and n=1 when M is an element thatbelongs to Group
 10. 13. A light-emitting device comprising: a firstelectrode; an insulating layer covering an end portion of the firstelectrode; a layer comprising an organometallic complex over the firstelectrode and the insulating layer; and a second electrode over thelayer comprising the organometallic complex, wherein the organometalliccomplex comprises a structure represented by a general formula (9),

wherein each of R²⁵ to R³⁰ represents any one of hydrogen, an alkylgroup, a halogen, a trifluoromethyl group, and an alkoxy group, andwherein M represents an element that belongs to Group 9 or Group
 10. 14.The light-emitting device according to claim 13, wherein M is iridium.15. The light-emitting device according to claim 13 further comprising atransistor electrically connected to the first electrode, wherein thefirst electrode is provided over the transistor.
 16. The light-emittingdevice according to claim 15, wherein the transistor comprises: asemiconductor film; and a gate electrode over the semiconductor film.17. An electronic appliance comprising the light-emitting deviceaccording to claim 13, wherein the electronic appliance is one selectedfrom the group consisting of a computer, a telephone set, and atelevision set.
 18. The light-emitting device according to claim 13,wherein the organometallic complex is represented by a general formula(10),

wherein L represents a monoanionic ligand, and wherein n=2 when M is anelement that belongs to Group 9, and n=1 when M is an element thatbelongs to Group 10.